Публикации

213bi production and complexation with new picolinate containing ligands / I. L. Sinenko, T. P. Kalmykova, D. V. Likhosherstova et al. // Journal of Radioanalytical and Nuclear Chemistry. — 2019. — Vol. 321, no. 2. — P. 531–540. Binding of bismuth cation with two newly synthesized picolinate containing acyclic (L1) and macrocyclic (L2) ligands was studied. Both ligands demonstrate complex formation with Bi3+ under ambient conditions with high complexation constants. Serum stability of the complexes was investigated in serum protein excess of 10- and 100-times. Experiments with no-carrier-added radiobismuth (207Bi and 213Bi) were performed. A one-column 225Ac/213Bi generator system, based on Ac resin (Triskem Inc.), was tested. The overall yield of 213Bi was exceeding 85% with 225Ac breakthrough below 10−4%. [ DOI ]

Benzoazacrown compound: a highly effective chelator for therapeutic bismuth radioisotopes / E. V. Matazova, B. V. Egorova, E. A. Konopkina et al. // MedChemComm. — 2019. [ DOI ]

Chemoselective detection of ag+ in purely aqueous solution using fluorescence "turn-on" probe based on crowm-containing 4-methoxy-1,8-naphthalimide / P. A. Panchenko, A. S. Polyakova, Y. V. Fedorov, O. A. Fedorova // Mendeleev Communications. — 2019. — Vol. 29. — P. 155–157. [ DOI ]

Donor–acceptor (e)-2-(2-(2,2'-bithiophen-5-yl)vinyl)benzo[d]thiazole: synthesis, optical, electrochemical studies and charge transport characteristics / S. D. Tokarev, Y. A. Sotnikova, A. V. Anisimov et al. // Mendeleev Communications. — 2019. — Vol. 29, no. 5. — P. 567–569. Condensation of 2-methylbenzothiazole with 2,2'-bithiophene-5-carbaldehyde affords the title compound, a new chromophore. This compound was used for the doping of poly[9,9bis(6diethoxylphosphorylhexyl)fluorene], and the obtained composites demonstrated high electron mobility (1.50×10–4 cm2 V–1 s–1) in contrast to dopant-free matrixes. [ DOI ]

Intramolecular electron transfer in cu(ii) complexes with aryl-imidazo-1,10-phenanthroline derivatives: experimental and quantum chemical calculation studies / O. A. Fedorova, S. D. Tokarev, N. E. Shepel et al. // New Journal of Chemistry. — 2019. — Vol. 43, no. 6. — P. 2817–2827. 1H-imidazo[4,5-f][1,10]phenanthrolines containing phenyl- (1), 4-(N,N-dimethylamino)phenyl- (2), 4-(azadithiacrownether) phenyl- (3) 3,4-dimethoxyphenyl- (4) and 2,2’-bithiophen-5-yl- (5) were synthesized and their Cu(II) complexes were studied to determine the effect of substituent, geometry of complex and solvent nature on the spectral and redox properties of the copper complexes. It was found that in case of 4-(N,N-dimethylamino)phenyl- and 4-(azadithiacrownether) phenyl substituents the formation of L2Cu2+ complex of pseudo-tetrahedral geometry causes the appearance of an intense metal-to-ligand charge transfer (MLCT) band at the visible region and induces a positive shift in the reduction potential providing the occurrence of autoreduction of Cu(II). Density functional theory (DFT) and its extension to time dependent density functional theory (TD-DFT) were performed to study the molecular structure, electronic and spectroscopic properties of copper with the 4-(N,N-dimethylamino)phenyl-1H-imidazo[4,5-f][1,10]phenanthroline ligand (2). The calculation results are in agreement with those obtained from optical measurements. Electrochemical study showed that the autoreduction is observed when Cu2+/Cu+ transfer and oxidation of ligand occur at the closed electrochemical condition. [ DOI ]

Out-cage metal ion coordination by novel benzoazacrown bisamides with carboxyl, pyridyl and picolinate pendant arms / A. D. Zubenko, B. V. Egorova, S. N. Kalmykov et al. // Tetrahedron. — 2019. — Vol. 75. — P. 2848–2859. [ DOI ]

Regioselective [2+2] photocycloaddition reaction of 2-(3,4-dimethoxystyryl)quinoxaline in solution / O. Fedorova, A. E. Saifutyarova, E. N. Gulakova et al. // Photochemical and Photobiological Sciences. — 2019.

Self-sorting processes in a stimuli-responsive supramolecular systems based on cucurbituril, cyclodextrin and bisstyryl guests / O. A. Fedorova, E. Y. Chernikova, S. V. Tkachenko et al. // JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY. — 2019. We report a four-component mixture comprising bisstyryl dyes, HP-β-CD and CB[7] that undergoes self-sorting in aqueous solution based on ion–dipole, electrostatic, charge–transfer interactions, as well as the hydrophobic effect. The formation of 1:1 and 1:2 complexes between the bisstyryl guests and HP-β-CD, CB[7] has been confirmed by optical and NMR spectroscopy as well as ESI-MS data. The studied supramolecular systems are stimuli responsive. Thus, protonation of bisstyryl dye based on pyridine heterocyclic residue leads to the destruction of its complexes with HP-β-CD. Whereas, complex of the bisstyryl dye with CB[7] based on N-methylpyridinium moiety can be replaced by Ba2+ cation. [ DOI ]

Spectral texture classification of high-resolution satellite images for the state forest inventory in russiaegor v. dmitriev, anton a. sokolov, vladimir v. kozoderov, hervé delbarre, petr g. melnik, and sergey a. donskoi / E. V. Dmitriev, A. A. Sokolov, V. V. Kozoderov et al. // Proc. SPIE 11149, Remote Sensing for Agriculture, Ecosystems, and Hydrology XXI, 111491J (21 October 2019). — 2019.

Synthesis of the fused heterocyclic systems via mallory photoreaction of arylthienylethenes / N. V. Dyachenko, A. V. Khoroshutin, S. Yulia et al. // Photochemical and Photobiological Sciences. — 2019. Photochemical oxidative cyclization of 2- and 3-thienylstilbenes (heterostilbenes) containing mono-, di- and trimethoxy groups in benzene ring or heterocyclic fragment results in the formation of isomeric thieno-annelated polycyclic aromatic compounds demonstrating optical properties differ from those of initial stilbene derivatives. The structures of cyclic products were evaluated via 1H and 13C NMR, HRMS, elemental analysis and X-ray crystallography. The research was aimed to study the effect of substituents in stilbene derivatives of thiophene as well as position of styryl fragment in thiophene nucleus on the occurring of photocyclization reaction. [ DOI ]

Synthesis, structure and metal ion coordination of novel benzodiazamacrocyclic ligands bearing pyridyl and picolinate pendant side-arms / P. A. Panchenko, A. D. Zubenko, E. Y. Chernikova et al. // New Journal of Chemistry. — 2019. [ DOI ]

Thiourea modified doxorubicin: A perspective ph-sensitive prodrug / O. O. Krasnovskaya, V. M. Malinnikov, N. S. Dashkova et al. // Bioconjugate Chemistry. — 2019. — Vol. 30, no. 3. — P. 741–750. A novel approach to the synthesis of pH-sensitive prodrugs has been proposed: thiourea drug modification. Resulting prodrugs can release the cytotoxic agent and the biologically active 2-thiohydantoin in the acidic environment of tumor cells. The concept of acid-catalyzed cyclization of thioureas to 2-thiohydantoins has been proven using a FRET model. Dual prodrugs of model azidothymidine, cytotoxic doxorubicin, and 2-thiohydantoin albutoin were obtained, which release the corresponding drugs in the acidic environment. The resulting doxorubicin prodrug was tested on prostate cancer cells and showed that the thiourea-modified prodrug is less cytotoxic (average IC50 ranging from 0.5584 to 0.9885 μM) than doxorubicin (IC50 ranging from 0.01258 to 0.02559 μM) in neutral pH 7.6 and has similar toxicity (average IC50 ranging from 0.4970 to 0.7994 μM) to doxorubicin (IC50 ranging from 0.2303 to 0.8110 μM) under mildly acidic conditions of cancer cells. Cellular and nuclear accumulation in PC3 tumor cells of Dox prodrug is much higher than accumulation of free doxorubicin. [ DOI ]

Черникова П. А., Шепель Н. Э., Федорова О. А. Исследование спектральных и комплексообразующих свойств моностирилового красителя c двухцепочечной ДНК // Успехи в химии и хим. технологии: Сб. науч. тр. РХТУ им. Д.И. Менделеева. — 2019. В данной работе изучено связывание красителя транс-4-[4-(метокси)стирил]-1-метилпиридиния йодида с двухцепочечной ДНК тимуса теленка в водном буферном растворе методами абсорбционной и эмиссионной спектроскопии с применением спектрофотометрического и спектрофлуорометрического титрования. Полученные данные были проанализированы с помощью уравнений МакГи и фон Хиппеля. Получены значения констант ассоциации. Измерены квантовые выходы флуоресценции свободного как лиганда, так и его ассоциата с молекулой ДНК.

Егорова Б. В., Федорова О. А., Калмыков С. Н. Катионные радионуклиды и лиганды для таргетных терапевтических радиофармпрепаратов // Russian Chemical Reviews. — 2019. — Т. 88, № 9. — С. 901–924. [ DOI ]

Краунсодержащие производные 4-метокси-1,8-нафталимида в качестве основы для разработки флуоресцентных РЕТ-хемосенсоров на катионы металлов / П. А. Панченко, Н. В. Лейчу, Ю. В. Федоров, О. А. Федорова // Макрогетероциклы. — 2019. [ DOI ]

Бахарева А. А., Зубенко А. Д., Федорова О. А. Разработка новых хелаторов для радиофармпрепаратов // Успехи в химии и химической технологии. — 2019. — Т. 33, № 7. — С. 18–20.

Пашанова А. В., Зубенко А. Д., Федорова О. А. Разработка рецепторов для биогенных катионов ca2+, cu2+ и zn2+ // Успехи в химии и химической технологии. — 2019. — Т. 33, № 7. — С. 21–23.

A nanohybrid for photodynamic therapy and fluorescence imaging tracking without therapy / L. Francés-Soriano, M. A. Zakharko, M. González-Béjar et al. // Chemistry of Materials. — 2018. — Vol. 30. — P. 3677–3682. [ DOI ]

Annelated tricyclic thiophenes and their photophysical properties / E. V. Lukovskaya, N. V. Dyachenko, A. V. Khoroshutin et al. // Mendeleev Communications. — 2018. — Vol. 28, no. 5. — P. 543–545. [ DOI ]

Complexation of a crown-substituted naphthalimide derivative with heavy metals in langmuir monolayers / I. I. Shepeleva, A. V. Shokurov, L. B. Bogdanova et al. // Russian Chemical Bulletin. — 2018. — Vol. 67, no. 12. — P. 2259–2261. It was demonstrated that, in contrast to a solution in an organic solvent, the relaxation of the excited state of a fluorophore moiety proceeds mainly radiationless upon the formation of naphthalimide fluoroionophore complexes with complementary cations in a monolayer at air-water interface. Apparently, this is due to the fact that at the air—water interface the distribution of the energy levels of molecular orbitals in the fluoroionophore complexes with cations change in such a way that relaxation of the excited state via charge transfer within the complex molecule remains possible. [ DOI ]

Design of hybrid macrocycles for selective binding and sensing of fluoride in aqueous solution / A. S. Oshchepkov, T. A. Shumilova, S. R. Namashivaya et al. // Journal of Organic Chemistry. — 2018.

Fret-based metal ion sensing by crown-containing bisstyryl dye / M. A. Ustimova, A. Y. Lebedeva, Y. V. Fedorov et al. // New Journal of Chemistry. — 2018. — Vol. 42. — P. 7908–7913. Firstly ratiometric cation FRET system containing two binding centers of different selectivity towards metal ions has been studied. The chemosensor based on crown-containing bisstyryl dye demonstrates a distinct fluorescence changes upon interaction with Na+, Li+, Mg2+, Ca2+, Ba2+, H+, Hg2+, Ag+ perchlorates. The fluorometric response of the chemosensor is attributed to the cation-induced modulating of the FRET process from oxacrown ether donor part to the azadithiacrown ether acceptor part. [ DOI ]

Governing the dna-binding mode of styryl dyes by the length of their alkyl substituents – from intercalation to major groove binding / D. V. Berdnikova, N. I. Sosnin, O. A. Fedorova, H. Ihmels // Organic and Biomolecular Chemistry. — 2018. [ DOI ]

Kinetics and thermodynamics of dna processing by wild type dna-glycosylase endo iii and its catalytically inactive mutant forms / O. A. Kladova, L. N. Krasnoperov, N. A. Kuznetsov, O. S. Fedorova // Genes. — 2018. — Vol. 9, no. 4. — P. E190.

Modulation of photochromic properties of spirooxazine bearing sulfobutyl substituent by metal ions / Y. V. Fedorov, N. E. Shepel, A. S. Peregudov et al. // Journal of Photochemistry and Photobiology A: Chemistry. — 2018. A novel spirooxazine bearing sulfobutyl substituent on the indoline part of the molecule has been synthesized and its photochromic properties and complex formation with metal ions have been studied. Under UV light irradiation of colorless acetonitrile solution of spirooxazine the open merocyanine form having an absorption band in visible region of the spectrum with max=625 nm is generated. Thermal back reaction of merocyanine form to spirooxazine with the rate constant 1.10 s-1 at 298 K has been observed. Interaction of spirooxazine with Mg2+, Ca2+, Cd2+, Zn2+ or Pb2+ ions in the dark leads to the formation of complexes of merocyanine form demonstrating a visible absorption band shifted from 20 to 8 nm relative to the uncomplexed merocyanine form. The activation energy of metal-induced coloration process in the dark is in the range of 84-88 kJ mol-1 and does not depend on the nature of the metal ions. This suggests that the process of thermal ring opening of the spiro form is the rate limiting step of complex formation. The degree of conversion of spirooxazine to complexed merocyanine form strongly depends on metal ions nature and irradiation wavelength. [ DOI ]

Novel 18-crown-6-ether containing mono- and bisstyryl dyes derived from pyridine moiety as fluorescent dyes for non-covalent interaction with dna / A. Y. Lebedeva, O. A. Fedorova, V. B. Tsvetkov et al. // Dyes and Pigments. — 2018. — Vol. 157. — P. 80–92. Bisstyrylpyridine dyes 1 and 2, in which two styrylpyridine moieties are connected to each other through the oxo- or azacrown ether unit, and their monomer analogues 3 and 4 have been synthesized and spectroscopically characterized. The prepared bisstyryl dyes 1 and 2 are the rare example of bisstyryls constructed in tail-to-tail mode. The binding of dyes 1–4 with salmon DNA has been evaluated using the UV–vis, CD, fluorescence, highsensitivity differential scanning calorimetry, viscometric data and molecular modeling. The dyes were found to have negligible fluorescence in a buffer solution, but exhibited a significant emission increase upon binding to DNA. The results obtained are consistent with a groove binding mode between mono- and bisstyryls and DNA. [ DOI ]

Novel pyridine-containing azacrown-ethers for the chelation of therapeutic bismuth radioisotopes: complexation study, radiolabeling, serum stability and biodistribution / B. V. Egorova, E. V. Matazova, A. A. Mitrofanov et al. // Nuclear Medicine and Biology. — 2018. — Vol. 60. — P. 1–10. [ DOI ]

Photosensitive organic-inorganic hybrid materials for room temperature gas sensor applications / M. Rumyantseva, A. Nasriddinov, S. Vladimirova et al. // NANOMATERIALS. — 2018. — Vol. 8, no. 9. — P. 671–1–671–16. In this work, the hybrids based on nanocrystalline SnO2 or In2O3 semiconductor matrixes and heterocyclic Ru(II) complex are studied as materials for gas sensors operating at room temperature under photoactivation with visible light. Nanocrystalline semiconductor oxides are obtained by chemical precipitation with subsequent thermal annealing and characterized by XRD, SEM and single-point BET methods. The heterocyclic Ru(II) complex is synthesized for the first time and investigated by 1H NMR, 13C NMR APT, MALDI-MS analysis, and UV-Vis spectroscopy. The HOMO and LUMO energies of the Ru(II) complex are calculated from cyclic voltammetry data. The hybrid materials are characterized by TGA-MS analysis and EDX mapping. The optical properties of hybrids are studied by UV-Vis spectroscopy in the diffuse reflection mode. The investigation of spectral dependencies of photoconductivity of hybrid samples demonstrates that the role of organic dye consists in shifting the photosensitivity range towards longer wavelengths. Sensor measurements demonstrate that hybrid materials are able to detect NO2 in the concentration range of 0.25–2 ppm without the use of thermal heating under periodic illumination with even low-energy long-wavelength (red) light. [ DOI ]

Panchenko P. A., Fedorov Y. V., Fedorova O. A. Selective fluorometric sensing of hg2+ in aqueous solution by the inhibition of pet from dithia-15-crown-5 ether receptor conjugated to 4-amino-1,8-naphthalimide fluorophore // Journal of Photochemistry and Photobiology A: Chemistry. — 2018. — Vol. 364. — P. 124–129. [ DOI ]

Supramolecular tuning of energy transfer efficiency and direction in a bis-chromophoric styryl dye / D. V. Berdnikova, Y. V. Fedorov, O. A. Fedorova, J. Gediminas // Dyes and Pigments. — 2018. — Vol. 151. — P. 227–232. The control of the energy transfer (FRET) in a novel bischromophoric styryl(pyridinium) dye bearing two different crown ether residues is presented. Complexation of the dye with metal cations allows to tune the FRET efficiency without changing the transfer direction or to switch the FRET off, whereas protonation launches the FRET process in the opposite direction relative to the molecular structure. [ DOI ]

Захарко М. А., Панченко П. А., Федорова О. А. Изучение влияния природы спейсерной группы на эффективности переноса энергии в конъюгатах бактериохлорина и нафталимида // Успехи в химии и химической технологии. — 2018. — Т. 32, № 5. — С. 76–78.

КОМПЛЕКСЫ ru (ii) С ПРОИЗВОДНЫМИ 1h-ИМИДАЗО[4,5-f][1,10]ФЕНАНТРОЛИНА: СИНТЕЗ И ФИЗИКО-ХИМИЧЕСКИЕ СВОЙСТВА / С. Д. Токарев, Ю. А. Сотникова, Н. В. Дьяченко, О. А. Федорова // Успехи в химии и химической технологии. — 2018. — Т. 32, № 5. — С. 117–119.

Комплексообразование краун-замещенного производного нафталимида с тяжелыми металлами в монослоях Ленгмюра / И. И. Шепелева, А. В. Шокуров, Л. Б. Богданова и др. // Известия Академии наук. Серия химическая. — 2018. — № 12. — С. 2259–2261.

Зубенко А. Д., Карноухова В. А., Федорова О. А. Новые амидные бензоазакраун-соединения: синтез и свойства // Успехи в химии и химической технологии. — 2018. — Т. 32, № 7. — С. 12–14.

Зубенко А. Д., Бахарева А. А., Федорова О. А. Разработка компонентов радиофармпрепаратов на основе пиридинсодержащих азакраун-соединений // Успехи в химии и химической технологии. — 2018. — Т. 32, № 5. — С. 35–37.

СИНТЕЗ ФОТОХРОМНЫХ ПРОИЗВОДНЫХ ХИНОКСАЛИНА / А. Э. Сайфутярова, Е. О. Гуськова, Е. Н. Гулакова, О. А. Федорова // Успехи в химии и химической технологии. — 2018. — Т. 32, № 5. — С. 112–114.

Синтез fret-пары нафталимид-флуоресцеин и изучение процесса переноса энергии в системе / П. А. Игнатов, М. А. Захарко, П. А. Панченко, О. А. Федорова // Успехи в химии и химической технологии. — 2018. — Т. 32, № 5. — С. 91–93.

Синтез и сенсорные свойства производного дитиакраунсодержащего 4-метоксинафталимида / А. С. Полякова, П. А. Панченко, Ю. В. Федоров, О. А. Федорова // Успехи в химии и химической технологии. — 2018. — Т. 32, № 7. — С. 80–82.

Зубенко А. Д., Пашанова А. В., Федорова О. А. Синтез новых бензодиазакраун-эфиров с различным типом хелатирующих групп // Успехи в химии и химической технологии. — 2018. — Т. 32, № 5. — С. 88–90.

A novel bacteriochlorin–styrylnaphthalimide conjugate for simultaneous photodynamic therapy and fluorescence imaging / P. A. Panchenko, M. A. Grin, O. A. Fedorova et al. // Physical Chemistry Chemical Physics. — 2017. — Vol. 19. — P. 30195–30206. [ DOI ]

Controlling photophysics of styrylnaphthalimides through tict, fluorescence and e,z-photoisomerization interplay / P. A. Panchenko, A. N. Arkhipova, O. A. Fedorova et al. // Physical Chemistry Chemical Physics. — 2017. — Vol. 19, no. 3. — P. 1244–1256. The photophysical properties of naphthalimide dyes NI1–3 with electron releasing 4-methoxy- (NI1), 3,4-dimethoxystyryl- (NI2) and dimethylaminostyryl (NI3) groups are examined in a variety of protic and aprotic solvents. All compounds demonstrate positive solvatochromism in the steady-state absorption and fluorescence spectra. The analysis of the dependence of the Stokes shift on the polarity of the solvent using the Lippert–Mataga equation allowed us to determine the change in the dipole moment upon excitation. The obtained data correspond to the formation of highly polar charge transfer states. Based on the transient absorption spectra and time-resolved fluorescence measurements, the presence of two different emissive states was definitely proved. The primarily formed planar Local Excited (LE) state dominates in non-polar solvents like cyclohexane and toluene where it relaxes mostly through fluorescence and E,Z-isomerisation pathways. In polar solvents, an alternative relaxation channel emerges that consists of twisting around single bond between styryl and naphthalimide fragments, which leads to the formation of a Twisted Intramolecular Charge Transfer (TICT) state. The factors affecting the fluorescence of TICT states are discussed. The observed spectral effects are rationalized using quantum-chemical calculations, X-ray data and NMR spectroscopy. [ DOI ]

H2s sensing by hybrids based on nanocrystalline sno2 functionalized with cu(ii) organometallic complexes: The role of the ligand platform / M. Rumyantseva, E. Makeeva, A. Gaskov et al. // NANOMATERIALS. — 2017. — Vol. 7, no. 11. — P. 384(1)–384(16). This paper deals with the functionalization of nanocrystalline SnO2 with Cu(II) complexes with organic ligands, aimed at the improvement of sensor selectivity towards gas molecules. For the synthesis of metalorganic/SnO2 hybrid material complexes of Cu(II) with phthalocyanine, porphyrinines, bipyridine and azadithiacrown etherwere used. The analysis of gas sensor properties showed the possibility of increasing the sensitivity and selectivity of hybrid materials in H2S detection due to the electron transfer from SnO2 to an adsorbed organic molecule, which changes during the interaction between H2S and Cu(II) ions. [ DOI ]

Light-induced piston nanoengines: ultrafast shuttling of a styryl dye inside cucurbit[7]uril / E. Y. Chernikova, D. V. Berdnikova, Y. V. Fedorov et al. // Physical Chemistry Chemical Physics. — 2017. — Vol. 19, no. 38. — P. 25834–25839. The combination of photoactive styryl(pyridinium) dyes and cucurbit[7]uril (CB[7]) in an integrated supramolecular system allowed us to design a novel high speed molecular machine based on the fully reversible shuttling motion of the dye inside the CB[7] host cavity. The driving force of this movement is the electrostatic potential change after the occurrence of intramolecular charge transfer in the excited state of the dye molecule that can be externally controlled by light. Steady-state and time-resolved optical spectroscopy as well as DFT calculations provided an unambiguous evidence for the ultrafast piston-like movement of the system between two states. The shuttling process occurs in the picosecond timescale and its bistability depends on the strength of the dye donor fragment. [ DOI ]

Naphthalimide-based polyammonium chemosensors for anions: study of binding properties and sensing mechanisms / A. S. Oshchepkov, R. R. Mittapalli, O. A. Fedorova, E. A. Kataev // Chemistry - A European Journal. — 2017. — Vol. 23, no. 40. — P. 9657–9665. Abstract New naphthalimide-based receptors for anions have been synthesized. Efficient synthetic routes have been discovered to functionalize the naphthalimide core with branched polyamines. Binding and sensing properties of the receptors were studied by potentiometric, NMR and fluorescence titrations. The receptors bind selectively to the pyrophosphate anion in buffered aqueous solutions. The receptors with more than six amine groups in the structure demonstrated the highest affinities for pyrophosphate. The fluorescence response towards anions was found to be dependent on the position of the amine groups relative to the naphthalimide core, and on the pH of the buffered solution. Three sensing mechanisms have been found that explain fluorescence responses of receptors towards anions in an aqueous solution. [ DOI ]

New copolymer gels based on n,n-dimethylacrylamide and crown-containing allyl derivative of 1,8-naphthalimide as optical sensors for metal cations in an organic medium / M. V. Oshchepkova, M. S. Oshchepkov, O. A. Fedorova et al. // Doklady Physical Chemistry. — 2017. — Vol. 476, no. 2. — P. 181–185. [ DOI ]

Olga F., Yuri F., Vladimir L. Photochromic crown ethers // Photon-Working Switches. — Springer, 2017. — P. 345–363.

Potentiometric studies of complex formation of amidopyridine macrocycles bearing pendant arms with proton and heavy metal ions in aqueous solution / Y. V. Fedorov, O. A. Fedorova, S. N. Kalmykov et al. // Polyhedron. — 2017. — Vol. 124. — P. 229–236. A novel pyridine-azacrown ether amide macrocycles comprising pyridine or carboxylic pendant arms were synthesized. The protonation constants of the compounds and the stability constants of their complexes with a wide range of metal ions (Ag+, Cu2+, Zn2+, Cd2+, Ni2+, Pb2+, Y3+, Eu3+, Lu3+) were determined by potentiometric method. The different complexes of macrocycles with cations, including HML, ML and ML(OH)n were found to form. The increase of the stability of the complexes provides the presence of carboxyl substituents in pyridineazacrown ether amide macrocycles; the values for the Cu2+, Ni2+ and Pb2+ complexes of ligand containing three carboxylic arms are exceptionally high. Single crystal structures of a few complexes with Cu2+ and Pb2+ were determined. In all complexes, the metal centre exhibit a strong coordination with amine N-atoms and arm’s ligand groups. The rigid structure of pyridine-2,6-dicarbamide fragment and an open macrocyclic cavity provide a possibility to fast kinetics of complex formation. [ DOI ]

Protonation-gated dual photochromism of a chromene–styryl dye hybrid / D. V. Berdnikova, T. Paululat, G. Jonusauskas et al. // Organic Letters. — 2017. — Vol. 19, no. 20. — P. 5633–5636. [ DOI ]

Regio- and stereoselective [2+2] photocycloaddition in ba2+ templated supramolecular dimers of styryl-derivatized aza-heterocycles / D. V. Berdnikova, T. M. Aliyeu, S. Delbaere et al. // Dyes and Pigments. — 2017. — Vol. 139. — P. 397–402. The regio- and stereoselective [2+2] photocycloaddition of 15-crown-5-containing styrylheterocycles resulting in formation of only one cyclobutane isomer out of eleven possible is described. It was shown that the cycloaddition takes place solely in the case of the supramolecular preorganization of the reactive molecules provided by both π–π stacking interaction of the heterocyclic fragments and sandwich-type coordination of the crown ether residues by the barium cation. The results point out the importance of the supramolecular approach for the synthesis of cyclobutane derivatives with desired structure and conformation. [ DOI ]

Relationship between the photochromic and fluorescent properties of 4-styryl derivatives of n-butyl-1,8-naphthalimide / A. N. Arkhipova, P. A. Panchenko, Y. V. Fedorov, O. A. Fedorova // Mendeleev Communications. — 2017. — Vol. 27, no. 1. — P. 53–55. [ DOI ]

Synthesis of 4-nitro-n-phenyl-1,8-naphthalimide annulated to thia- and azacrown ether moieties / A. S. Oshchepkov, M. S. Oshchepkov, A. N. Arkhipova et al. // SYNTHESIS-STUTTGART. — 2017. — Vol. 49. — P. 2231–2240. [ DOI ]

Synthesis, optical characteristics and complex formation of molecular receptors based on 1,8-naphthalimide derivatives in solution and in composition of hybrid tin dioxide nanoparticles / A. N. Arkhipova, P. A. Panchenko, N. E. Schepel et al. // Макрогетероциклы. — 2017. — Vol. 10, no. 1. — P. 84–93. [ DOI ]

Tandem intramolecular cyclisation/1,3-aryl shift in n-(4,4-diethoxybutyl)-1-arylmethanimines (kazan reaction): Synthesis of 3-benzylidene-1-pyrrolines / A. V. Smolobochkin, A. S. Gazizov, A. S. Melyashova et al. // RSC advances. — 2017. — Vol. 7. — P. 50955–50960. In this article, a novel tandem reaction, which transforms N-(4,4-diethoxybutyl)imines into 3-arylidene-1- pyrrolines, is described. The substrate scope of the starting acetals includes arenes with electron-donating and withdrawing groups. The X-ray study of products confirmed the E-stereochemistry of the double bonds formed. The best yields (99%) are found in boiling xylene in the presence of TsOH (or 2-nitroresocinol) during 40 (50) hours. The study of substituents effect on the course of the reaction revealed that cascade process takes place, combining acid-catalyzed intramolecular cyclization of N-(4,4- diethoxybutyl)imines and unusual 1,3-sigmatropic shift of the aryl fragment. Cyclic imines that are formed in high/excellent yields are of interest both from the viewpoint of their biological activity and synthetic usefulness. [ DOI ]

Изучение переноса энергии в супрамолекулярной системе на основе нафтилкукурбит[6]урила и стирилового красителя / А. И. Грачев, Е. Ю. Черникова, С. В. Ткаченко и др. // Успехи в химии и химической технологии. — 2017. — Т. 31, № 12. — С. 39–41.

Харченко Д. С., Панченко П. А., Федорова О. А. Комплексообразующие свойства n-фенилазадитиа-15-краун-5-эфирсодержащего производного 4-аминонафталимида с катионами металлов // Успехи в химии и химической технологии. — 2017. — Т. 31, № 12. — С. 75–77.

Лебедева А. Ю., Черникова Е. Ю., Федорова О. А. Конкурентное взаимодействие бисстириловых красителей с кукурбит[7]урилом и двухцепочечной ДНК // Успехи в химии и химической технологии. — 2017. — Т. 31, № 12. — С. 60–62. В данной работе изучено образование супрамолекулярных комплексов дибензо- и диаза-18-краун-6-содержащих бисстириловых красителей с кукурбит[7]урилом и двухцепочечной ДНК тимуса теленка в буферном растворе. Проведено исследование конкурентных взаимодействий в тройной системе ДНК-краситель-кукурбит[7]урил. Изучение процессов комплексообразования проводилось с помощью методов спектрофотометрического и флуориметрического титрований. https://elibrary.ru/item.asp?id=30628179.

Новые сополимерные гели на основе n,n-диметилакриламида и краунсодержащего производного 1,8-нафталимида в качестве оптических сенсоров на катионы металлов в органичеких средах / М. В. Ощепкова, М. С. Ощепков, О. А. Федорова и др. // Доклады Академии наук. — 2017. — Т. 476, № 5. — С. 530–534. Синтезированы новые сополимерные гели на основе N,N-диметилакриламида и краунсодержаще- го аллильного производного 1,8-нафталимида, обладающие интенсивной флуоресценцией в ви- димой области спектра. Изучено влияние серии катионов металлов на оптические свойства флуо- ресцентного мономера и его сополимерных гелей. Установлено, что такие гели обладают селек- тивностью оптического отклика в отношении связывания катионов щелочноземельных металлов в среде ацетонитрила. [ DOI ]

Разработка оптического сенсора на анионы на основе азометинового производного 1,8-нафталимида / П. А. Игнатов, М. А. Захарко, П. А. Панченко, О. А. Федорова // Успехи в химии и химической технологии. — 2017. — Т. 31, № 12. — С. 54–56.

Синтез бифункциональных производных бензоазакраун-соединений / А. Д. Зубенко, А. И. Станкова, А. С. Ощепков, О. А. Федорова // Успехи в химии и химической технологии. — 2017. — Т. 31, № 12. — С. 51–53.

Синтез и исследование оптических свойств конъюгата бактериохлорина и красителя на основе нафталимида для комбинированной фотодинамической терапии и флуоресцентной диагностики рака / М. А. Захарко, А. Н. Архипова, П. А. Панченко, О. А. Федорова // Успехи в химии и химической технологии. — 2017. — Т. 31, № 12. — С. 45–47.

Устимова М. А., Лебедева А. Ю., Федорова О. А. Синтез новых бисстириловых красителей // Успехи в химии и химической технологии. — 2017. — Т. 31. — С. 72–74. В данной работе были подобраны оптимальные условия синтеза и получен ряд новых бисстириловых красителей, в которых стириловые фрагменты связаны между собой алкильным линкером и располагаются относительно друг друга как голова-к-голове, голова-к-хвосту и хвост-к-хвосту. Структуры полученных соединений были подтверждены методами масс-спектрометрии, ЯМР-спектроскопии и элементного анализа.

Cation-dependent structural diversity of zinc(ii), calcium(ii) mono- andbinuclear complexes of aryl-imidazo-1,10-phenanthroline derivatives / S. Yulia, L. Elena, B. Alla et al. // Inorganica Chimica Acta. — 2016. — Vol. 445. — P. 103–109. The syntheses of azacrown-containing aryl-imidazophenanthroline by reaction of 1,10-phenanthroline- 5,6-dion with 4-(1.4.7.10-tetraoxa-13-azacyclopentadecan-13-yl)benzaldehyde producing the ligand 2 in high yield is described. Examination of their Zn(II), Ca(II) and mixed complexes by UV/Vis and NMR spectroscopy suggests electronic communication between the two metal centers of ligand 2. Stability constants, determined by spectrophotometric titration, indicate that the Zn(II) possesses higher affinity toward phenanthroline residue than Ca(II) and does not bind with azacrown-ether residue. This selectivity allows to prepare a mixed Zn(II)/Ca(II) complex.

Complex formation of pyridine-azacrown ether amide macrocycles with proton and heavy metal ions in aqueous solution / Y. V. Fedorov, O. A. Fedorova, A. Peregudov et al. // Journal of Physical Organic Chemistry. — 2016. — Vol. 29, no. 5. — P. 244–250. [ DOI ]

Complexation of bi3+, ac3+, y3+, lu3+, la3+ and eu3+ with benzo-diaza-crown ether with carboxylic pendant arms / B. V. Egorova, M. S. Oshchepkov, Y. V. Fedorov et al. // Radiochimica Acta. — 2016. — P. 1–11. [ DOI ]

Extraction studies of heavy metal ions employing benzothiaoxacrown compounds / T. Tsend-Ayush, M. Wenzel, K. Gloe et al. // Solvent Extraction Research and Development. — 2016. — Vol. 23, no. 1. — P. 31–41. Benzothiaoxacrown compounds with different numbers of sulfur and oxygen donor atoms (between 4 to 7 donors) dissolved in an organic diluent selectively extract the soft metal ions Ag(I) and Hg(II) from a mixture of Co(II), Ni(II), Cu(II), Zn(II), Ag(I) and Hg(II) present in an aqueous phase. Generally, the extraction efficiency depends on the specific structure of the benzothiaoxacrowns, on the organic diluent employed, as well as on the counter ion present in the aqueous phase. High extractions of Ag(I) and Hg(II) were achieved with all ligands from perchlorate and picrate aqueous media into nitrobenzene organic solutions. In the case of Cu(I) the extraction is significant lower; only ligand 5 with the O2S4 donor atom set gives a moderate extractability. The composition of the extracted complexes depends on the crown ring size and ranges from 1:1 to 1:2 (M:L). Polarographic, UV-Vis and ESI mass spectrometric studies provide a further insight into the complex formation behavior. [ DOI ]

Investigation of the photoinduced energy transfer in the supramolecular complexes of styryl dyes / A. Y. Lebedeva, T. N. Leontyev, M. S. Oshchepkov et al. // Russian Chemical Bulletin. — 2016. — Vol. 65, no. 10. — P. 2381–2387. Self-assembly of monostyryl dye of benzothiazole series with symmetric and asymmetric bisstyryl dyes based on dibenzo-18-crown-6 ether has been studied by optical and NMR spectroscopies. The photoinduced energy transfer between mono- and bisstyryl dyes in supramolecular assembly has been analyzed. The cascade energy transfer in the supramolecular complex of monostyryl dye with asymmetric bisstyryl dye has been suggested. [ DOI ]

Multiparameter molecular sensor based on a compound containing tetrathiafulvalenium, thiophene and piridine fragments / E. V. Lukovskaya, J. A. Sotnikova, A. A. Bobyleva et al. // Mendeleev Communications. — 2016. — Vol. 26, no. 3. — P. 202–204.

Multistep assembling via intermolecular interaction between (bis)styryl dye and cucurbit[7]uril: Spectral effects and host sliding motion / E. Y. Chernikova, S. V. Tkachenko, O. A. Fedorova et al. // Dyes and Pigments. — 2016. — Vol. 131. — P. 206–214. Abstract The host–guest interaction between bis(styryl)pyridinium dye (BSP) and cucurbit[7]uril (CB[7]) was studied by means of optical spectroscopy, 1H and 2D (COSY, ROESY, DOSY) NMR spectroscopy and electrospray ionization mass spectrometry in different microenvironment (aqueous or phosphate buffer solution). The CB[7] macrocycles bind to BSP dye in a stepwise manner thus forming higher stoichiometric complexes such as (H+)2–BSP–(CB[7])3 in aqueous or BSP–(CB[7])3 in buffered solution. In the case of aqueous solution, complex formation is accompanied by the host-assisting protonation of the anilino-type BSP nitrogen atoms, that causes a pronounced effect on its spectral properties. Stimuli-responsive sliding movements of the CB[7] macrocycles along the stalk of dye molecule were also observed. [ DOI ]

Regiospecific photocyclization of mono- and bis-styryl-substituted n-heterocycles: A synthesis of dna-binding benzo[c]quinolizinium derivatives / T. M. Aliyeu, D. V. Berdnikova, O. A. Fedorova et al. // Journal of Organic Chemistry. — 2016. — Vol. 81, no. 19. — P. 9075–9085. [ DOI ]

Synthesis and spectral properties of fluorescent dyes based on 4-styryl-1,8-naphthalimide / P. A. Panchenko, A. N. Arkhipova, M. A. Zakharko et al. // Russian Chemical Bulletin. — 2016. — Vol. 65, no. 10. — P. 2444–2451. [ DOI ]

Utilizing a ph-sensitive dye in the selective fluorescent recognition of sulfate / A. M. Agafontsev, T. A. Shumilova, P. A. Panchenko et al. // Chemistry - A European Journal. — 2016. — Vol. 22, no. 42. — P. 15069–15074. A receptor containing amidopyrrole binding subunits and free amino groups, conjugated to a naphthalimide dye, has been designed and synthesized. The intrinsic selectivity of the binding motif for phosphate present in DMSO completely disappears in 10% DMSO aqueous buffer at pH 3.6, at which the receptor is protonated. The electrostatic interactions between the receptor and an anion start to dominate, thus leading to selectivity for sulfate. The ability of the HSO4- anion to transfer the proton to the amino group during the recognition event suppresses the photoinduced electron transfer (PET) on the dye, resulting in a selective turn-on fluorescent response. The choice of pH of the solution for sensing is dictated by the pKa value of the dye. [ DOI ]

ИССЛЕДОВАНИЕ СПЕКТРАЛЬНЫХ И КОМПЛЕКСООБРАЗУЮЩИХ СВОЙСТВ КРАУНСОДЕРЖАЩЕГО БИССТИРИЛОВОГО КРАСИТЕЛЯ С МОЛЕКУЛАМИ-КОНТЕЙНЕРАМИ / А. Ю. Лебедева, C. В. Ткаченко, Е. Ю. Черникова и др. // Успехи в химии и химической технологии. — 2016. — Т. 30, № 11. — С. 36–38. В данной работе синтезирован и охарактеризован новый бисстириловый краситель, содержащий фрагмент 18- краун-6-эфира. Исследовано образование супрамолекулярных комплексов гость-хозяин данного красителя с гидроксипропил-β-циклодекстрином и кукурбит[7]урилом в буфере. Изучение процесса комплексообразования проводилось с помощью методов оптической спектроскопии и масс-спектрометрии высокого разрешения. В свободном бисстириловом красителе обнаружено протекание фотоиндуцированного переноса энергии.

Изучение фотоиндуцированного переноса энергии в супрамолекулярных ансамблях стириловых красителей / А. Ю. Лебедева, Т. Н. Леонтьев, М. С. Ощепков и др. // Известия Академии наук. Серия химическая. — 2016. — № 10. — С. 2381–2387.

Ольга Ф. Невидимые машины завоёвывают мир // Наука и жизнь. — 2016. — № 12. — С. 2–7.

Псевдоротаксановые структуры на основе тиофенсодержащих производных дибензо-24-краун-8-эфиров / Е. В. Луковская, А. А. Космачева, О. А. Федорова и др. // Макрогетероциклы. — 2016. — Т. 9, № 1. — С. 89–95.

Синтез новых стириловых производных 1,8-нафталимида / М. А. Захарко, А. Н. Архипова, П. А. Панченко, О. А. Федорова // Успехи в химии и химической технологии. — 2016. — Т. 30, № 11. — С. 33–35.

Cation-dependent spectral properties of fluorescent complexon based on 1,8-naphthalimide with pet mechanism of optical response / P. A. Panchenko, V. V. Park, O. A. Fedorova et al. // Russian Chemical Bulletin. — 2015. — Vol. 64, no. 8. — P. 1871–1876. Complexation of 4-amino-1,8-naphthalimide derivative containing an aza-15-crown-5 ether receptor unit in the N-aryl substituent at the imide nitrogen atom of the naphthalimide core with alkaline earth metal cations was studied using optical and NMR spectroscopy. The binding of the cations with crown ether receptors was accompanied by signifacant fluorescence enhancement of naphthalimide moiety caused by the inhibition of the photoinduced electron transfer (PET) process. An increase in the cation radii on going from Mg2+ to Ca2+ to Ba2+ leads to a decrease in the complex stability and an increase in the quantum yield of its fluorescence. [ DOI ]

Dna–ligand interactions gained and lost: light-induced ligand redistribution in a supramolecular cascade / D. V. Berdnikova, T. M. Aliyeu, T. Paululat et al. // Chemical Communications. — 2015. — Vol. 51. — P. 4906–4909. [ DOI ]

Effect of light irradiation on the gas sensor characteristics of the sno2 and zno modified by tetrathiafulvalene derivative / E. V. Lukovskaya, O. A. Fedorova, Y. A. Glazova et al. // Organic Photonics and Photovoltaics. — 2015. — Vol. 3, no. 1. — P. 54–63. We present the description of the synthesis and characteristics of the SnO2 and ZnO modified by novel tetrathiafulvalene (TTF) derivative. The analysis of the gas sensor properties showed the possibility of light photoactivation of modified semiconductor gas sensor due to the electron transfer from LUMO of TTF molecule to the conduction band of semiconductor matrix. [ DOI ]

Fret versus pet: ratiometric chemosensors assembled from naphthalimide dyes and crown ethers / P. A. Panchenko, Y. V. Fedorov, O. A. Fedorova, J. Gediminas // Physical Chemistry Chemical Physics. — 2015. — Vol. 17, no. 35. — P. 22749–22757. Novel bi-chromophoric naphthalimide derivatives containing benzo-15-crown-5 and N-phenyl-aza-15- crown-5 receptor moieties BNI2 and BNI3 were designed and prepared. Significant Fo ¨rster resonance energy transfer (FRET) from donor (D) amido-naphthalimide to acceptor (A) amino-naphthalimide chromophores as well as photoinduced electron transfer (PET) between the N-aryl receptor and amido- naphthalimide fragment was revealed by the steady-state and time-resolved UV/Vis absorption and fluorescence spectroscopy. Upon the addition of alkaline-earth metal perchlorates to an acetonitrile solution of ligands, FRET mediated fluorescence enhancement was observed, which was a result of inhibition of the PET competitive deactivation pathway. The studied compounds provide an opportunity to register a two-channel fluorescence response upon selective excitation of either of the photoactive units and, thus, might be of interest as ratiometric probes. [ DOI ]

Fluorescent cryogels based on copolymers of n,n-dimethylacrylamide and allyl derivatives of 1,8-naphthalimide / M. V. Oshchepkova, A. S. Oshchepkov, O. E. Zaborina et al. // Polymer Science, Series B. — 2015. — Vol. 57, no. 6. — P. 631–637. New polymer cryogels based on N,Ndimethylacrylamide and allyl derivatives of 1,8naphthalim ide have been synthesized. They have intense fluorescence in the visible region of the spectrum. The influence of synthesis conditions on the properties of the resulting products has been studied. The maximum yield of the gel fraction and the minimum degree of swelling of the crosslinked polymer are observed during the low temperature (–20oC) synthesis of cryogels. Their fluorescence depends on the monomer content reaching the maximum value at concentrations of N,Ndimethylacrylamide and a fluorophorecontaining monomer of 1.0 and 1.0 × 10–3 mol/L, respectively. [ DOI ]

Interaction of crown ether-annelated styryl dyes with double-stranded dna / D. V. Berdnikova, O. A. Fedorova, E. V. Tulyakova et al. // Photochemistry and Photobiology. — 2015. — Vol. 91, no. 3. — P. 723–731. [ DOI ]

Isomeric naphthalimides bearing pyran units: Insight into mutual relation between structure and photochromic properties / O. A. Fedorova, A. N. Sergeeva, P. A. Panchenko et al. // Journal of Photochemistry and Photobiology A: Chemistry. — 2015. — Vol. 303. — P. 28–35. [ DOI ]

Photoinduced guest transformation promotes translocation of guest from hydroxypropyl-beta-cyclodextrin to cucurbit 7 uril / Y. V. Fedorov, S. V. Tkachenko, E. Y. Chernikova et al. // Chemical Communications. — 2015. — Vol. 51, no. 7. — P. 1349–1352. [ DOI ]

Pre-steady-state kinetic and structural analysis of interaction of methionine γ-lyase from citrobacter freundii with inhibitors / N. A. Kuznetsov, N. G. Faleev, A. A. Kuznetsova et al. // Journal of Biological Chemistry. — 2015. — Vol. 290. — P. 671–681. [ DOI ]

Synthesis of 4-nitro-and 4-aminophenylazacrown ethers / A. S. Oshchepkov, M. S. Oshchepkov, A. V. Anisimov, O. A. Fedorova // Макрогетероциклы. — 2015. — Vol. 8. — P. 290–293. [ DOI ]

МУЛЬТИКОМПОНЕНТНЫЕ МОЛЕКУЛЯРНЫЕ АНСАМБЛИ БИССТИРИЛОВОГО КРАСИТЕЛЯ С КУКУРБИТ[7]УРИЛОМ: СТРОЕНИЕ И СПЕКТРАЛЬНЫЕ СВОЙСТВА / С. В. Ткаченко, Е. Ю. Черникова, С. Минковска и др. // Успехи в химии и химической технологии. — 2015. — Т. 29, № 7. — С. 117–120. Методами оптической и ЯМР спектроскопии было изучено взаимодействие по типу гость-хозяин симметричного бисстирилового красителя с кукурбит[7]урилом в водных растворах. Было установлено, что процесс комплексообразования в водной среде сопровождается протонированием лиганда и приводит к образованию четырехкомпонентного комплекса (Н+)2-БСП-(CB[7])3.

Ощепков А. С., Ощепков М. С., Федорова О. А. Модельные платформы для создания оптических сенсоров // Успехи в химии и химической технологии. — 2015. — Т. 29, № 1. — С. 96–98.

Новые комплексоны для катионов тяжелых металлов и радионуклидов / Ф. Ольга, З. Анастасия, О. Максим и др. // Медицина: целевые проекты. — 2015. — № 22. — С. 67–69.

Оптические и электрохимические характеристики краун- и тиофенсодержащих производных 1h-имидазо[4,5-f]фенантролина и их комплексообразование с катионом ca2+ / Ю. А. Сотникова, Е. В. Пахова, С. Д. Токарев и др. // Успехи в химии и химической технологии. — 2015. — Т. 29. — С. 99–101.

Разработка подходов к синтезу краунсодержащих полигетероциклических мультипараметрических сенсоров на катионы тяжелых и переходных металлов / С. Д. Токарев, Ю. А. Сотникова, Е. В. Луковская и др. // Успехи в химии и химической технологии. — 2015. — Т. 29. — С. 102–105.

Леонтьев Т. Н., Лебедева А. Ю., Федорова О. А. Синтез и изучение спектральных свойств стириловых красителей на основе бензотиазола и пиридина // Успехи в химии и химической технологии. — 2015. — Т. 29, № 7 (166). — С. 114–116.

Ощепков А. С., Ощепкова М. В., Федорова О. А. Синтез производных нафталимидов, содержащих рецепторный фрагмент на основе ди(гидроксиэтил)амина // Успехи в химии и химической технологии. — 2015. — Т. 29, № 1. — С. 93–95.

ФОТОИЗОМЕРИЗАЦИЯ КРАУН-СОДЕРЖАЩИХ БИССТИРИЛОВЫХ ЛИГАНДОВ В КОМПЛЕКСАХ С ГИДРОКСИПРОПИЛ-β-ЦИКЛОДЕСКТРИНОМ / С. В. Ткаченко, М. С. Ощепков, О. И. Цветкова и др. // Успехи в химии и химической технологии. — 2015. — Т. 29, № 7. — С. 121–123. Методами оптической спектроскопии было изучено взаимодействие по типу гость-хозяин дибензо- и диаза-18- краун-6-содержащих бисстириловых красителей с 2-гидроксипропил-β-циклодекстрином в водных растворах. Было установлено, что фотохимические свойства как самих исходных лигандов, так и их комплексов зависят от типа краун-эфирного фрагмента.

ФОТОХИМИЧЕСКАЯ ДИМЕРИЗАЦИЯ 2-(3,4-ДИМЕТОКСИСТИРИЛ)ХИНОКСАЛИНА / Ю. В. Никитина, Т. М. Алиев, Н. Э. Шепель и др. // Успехи в химии и химической технологии. — 2015. — Т. 29, № 7. — С. 111–113. Осуществлен синтез 2-(3,4-диметоксистирил)хиноксалина. С использованием методов оптической и ЯМР спектроскопии исследованы фототрансформации полученного соединения. Обнаружено, что фотолиз ацетонитрильных растворов субстрата светом длиной волны 365 нм приводит к протеканию фотореакции, основным продуктом которой становится тетразамещенный циклобутан.

An approach to the asymmetric synthesis of 18f-labeled analog of l-threo-3,4-dihydroxyphenylserine (6-l-threo-[18f]fdops) — a new radiotracer for visualization of norepinephrine transporters by positron emission tomography / O. S. Fedorova, V. V. Orlovskaya, V. I. Maleev et al. // Russian Chemical Bulletin. — 2014. — Vol. 63, no. 5. — P. 1169–1177. [ DOI ]

Effect of the chromophoric unit on the complex formation properties in the crown ether containing styryl dyes / L. Elena, G. Yulia, F. Yury et al. // Dyes and Pigments. — 2014. — Vol. 104. — P. 151–159. The benzo- and thieno-crown ethers containing styryl dyes have been designed and synthesized. The two series of the compounds were based on different combinations of the oxa- and azaoxa-crown ether fragments together with 2-benzovinyl- and thienylvinyl-benzothiazolium units. Their complexing, optical and electrochemical behaviors were characterized, while one and two dimensional NMR was employed to evaluate the structures of free and complexed ligands. The results of these studies showed that thienylvinyl derivatives display the poor ability for binding with metal ions through the crown ether moiety. The phenomenon was explained by the particular charge distribution in thienylvinyl derivatives preventing the interaction of chromophoric crown ethers with metal ions. [ DOI ]

Equilibrium between two degenerated forms during complexation of novel bis-crown containing bithiophene and alkanediammonium cations / A. A. Kosmacheva, E. V. Lukovskaya, O. A. Fedorova et al. // Макрогетероциклы. — 2014. — Vol. 7, no. 4. — P. 365–372. [ DOI ]

Panchenko P. A., Fedorova O. A., Fedorov Y. V. Fluorescent and colorimetric chemosensors for cations based on 1,8-naphthalimide derivatives: design principles and optical signalling mechanisms // Russian Chemical Reviews. — 2014. — Vol. 83, no. 2. — P. 155–182. [ DOI ]

Intra- and interlayer energy transfer in planar systems based on amphiphilic naphthalimide derivatives / S. L. Selector, L. B. Bogdanova, A. V. Shokurov et al. // Макрогетероциклы. — 2014. — Vol. 7, no. 3. — P. 311–320. The present work considers the possibility of increasing the information signal of thin-film sensitive element of the sensor based on amphiphilic crown substituted derivative of 4-(acylamino)-1,8-naphthalimide via employment of resonance photoexcitation energy transfer process. In such system, information signal is the fluorescence of acceptor fluorophore (4-alkylamino-1,8-naphthalimide), which is excited upon non-radiative transfer of the energy from excited donor fluorophore (crown containing derivative of 4-(acylamino)-1,8-naphthalimide), crown ether fragment of which is “occupied” by coordination interaction with specific cation and thus does not participate in rapid relaxation of the excitation by the photoinduced electron transfer mechanism. For realization of this goal, the synthesis of novel amphiphilic naphthalimide derivatives is carried out; conditions for obtaining of stable monolayers and Langmuir-Blodgett films based on them are studied. It is established that azadithiacrown substituted amphiphilic fluoroionophore in monolayers at air/mercury and silver perchlorate aqueous solutions interface retains the ability for efficient binding of Ag+ and Hg2+ known for its solutions. Described principle of generation of fluorescent signal using mixed monolayer containing the donor-acceptor couple allows one to increase the value of optical response of the monolayer to the presence of assessed cations by 2.5 times. However, the monolayer fluorescence intensity remains too low for practical application. In order to optimize the conditions of the energy transfer process in more practically important solid-state sensory elements we studied the mechanism of non-radiative photoexcitation energy transfer in the multilayer thin-film system based on amphiphilic naphthalimide derivatives obtained by Langmuir-Blodgett (LB) technique. It is shown that this problem can be solved by regulation of the distance between donor and acceptor layers of LBF. Optimal thickness of the separating layer of stearic acid, which for this system amounted to 7 nm, was determined experimentally. Obtained results open up new perspectives for increase of the information signal reading efficiency, which should find application in development of sensitive elements of sensor devices. [ DOI ]

Photoresponsive dendron-like metallocomplexes of the crown-containing styryl derivatives of 2,2 ’-bipyridine / N. E. Shepel, O. A. Fedorova, E. N. Gulakova et al. // Dalton Transactions. — 2014. — Vol. 43, no. 2. — P. 769–778. [ DOI ]

Planar supramolecular systems based on geometrical isomers of crown-containing oligothiophenes / S. L. Selektor, O. A. Fedorova, E. V. Lukovskaya et al. // Protection of Metals and Physical Chemistry of Surfaces. — 2014. — Vol. 50, no. 5. — P. 557–569. [ DOI ]

Regiospecific c-n photocyclization of 2-styrylquinolines / E. N. Gulakova, D. V. Berdnikova, T. M. Aliyeu et al. // Journal of Organic Chemistry. — 2014. — Vol. 79, no. 12. — P. 5533–5537. [ DOI ]

Spectroscopical study of bacteriopurpurinimide-naphthalimide conjugates for fluorescent diagnostics and photodynamic therapy / P. A. Panchenko, A. N. Sergeeva, O. A. Fedorova et al. // Journal of Photochemistry and Photobiology B: Biology. — 2014. — Vol. 133. — P. 140–144. [ DOI ]

Synthesis and complex formation of crown containing polyheterocyclic derivative - multiparametric sensor for metal cations / Y. A. Glazova, E. V. Lukovskaya, Y. V. Fedorov et al. // Макрогетероциклы. — 2014. — Vol. 7, no. 4. — P. 373–379. [ DOI ]

Synthesis of chromophoric crown-containing styryl derivative of terthiophene and its complexation with octane-1,8-diaminium diperchlorate / E. V. Lukovskaya, A. A. Kosmacheva, O. A. Fedorova et al. // Russian Journal of Organic Chemistry. — 2014. — Vol. 50, no. 4. — P. 552–558. [ DOI ]

Два подхода к синтезу бензотриаза-15- краун-5-эфира / А. Д. Мутасова, М. С. Ощепков, А. С. Ощепков, О. А. Федорова // Успехи в химии и химической технологии. — 2014. — Т. 28, № 9. — С. 80–82.

КОМПЛЕКСООБРАЗУЮЩИЕ СВОЙСТВА АЗАКРАУНСОДЕРЖАЩИХ БИССТИРИЛОВЫХ КРАСИТЕЛЕЙ В ПРИСУТСТВИИ МОЛЕКУЛ-КОНТЕЙНЕРОВ: ЦИКЛОДЕКСТРИНА И КУКУРБИТУРИЛА / С. В. Ткаченко, М. С. Ощепков, О. И. Цветкова и др. // Успехи в химии и химической технологии. — 2014. — Т. 28, № 9. — С. 86–90.

Молекулярные машины на основе супрамолекулярных систем / М. С. Ощепков, О. И. Цветкова, А. Ю. Лебедева и др. // Бутлеровские сообщения. — 2014. — Т. 39, № 10. — С. 1–22.

Новые тиофенсодержащие производные дибензо-24-краун-8-эфиров / А. А. Космачева, Е. В. Луковская, О. А. Федорова и др. // Успехи в химии и химической технологии. — 2014. — Т. 28, № 10. — С. 64–67.

Оптические сенсоры на катионы на основе производных 1,8-нафталимида, содержащие салицилидениминовый фрагмент / С. Д. Камагуров, П. А. Панченко, О. А. Федорова, Н. Э. Шепель // Успехи в химии и химической технологии. — 2014. — Т. 28, № 10 (159). — С. 56–59.

ПЛАНАРНЫЕ СУПРАМОЛЕКУЛЯРНЫЕ СИСТЕМЫ НА ОСНОВЕ ГЕОМЕТРИЧЕСКИХ ИЗОМЕРОВ, КРАУНИРОВАННЫХ ОЛИГОТИОФЕНОВ / С. Л. Селектор, О. А. Федорова, Е. В. Луковская и др. // Физикохимия поверхности и защита материалов. — 2014. — Т. 50. — С. 451–464. [ DOI ]

ПОЛИЯДЕРНЫЕ КОМПЛЕКСЫ КРАУН_СОДЕРЖАЩИХ МОНОСТИРИЛФЕНАНТРОЛИНОВ / Ю. В. Федоров, Н. Э. Шепель, О. Ю. Колосова и др. // Известия Академии наук. Серия химическая. — 2014. — № 10. — С. 2271–2280. Pезультаты исследований методами оптической и ЯМР%спектроскопии показали, что краунсодержащие стирилфенантролины в присутствии катионов металлов различ% ной природы способны к образованию молекулярных ансамблей, составом и структурой которых можно управлять с учетом закономерностей комплексообразования. Установ% лено, что металлокомплексы цинка и стирилфенантролинов являются флуоресцентны% ми лигандами для катионов металлов, которые могут координироваться со свободными краун%эфирными фрагментами стирилфенантролинов.

Планарные супрамолекулярные системы на основе изомерных краун-содержащих олиготиофенов / С. Л. Селектор, О. А. Федорова, Е. В. Луковская и др. // Физикохимия поверхности и защита материалов. — 2014. — Т. 50, № 5. — С. 557–569.

Разработка подходов к асимметрическому синтезу меченного фтором-18 аналога l-трео-3,4-дигидроксифенилсерина (6-l-трео-[18f]fdops) — нового радиотрейсера для визуализации транспортеров норэпинефрина методом позитронной эмиссионной томографии / О. С. Федорова, В. В. Орловская, В. И. Малеев и др. // Известия Академии наук. Серия химическая. — 2014. — Т. 63, № 5. — С. 1169–1177. [ DOI ]

Синтез 4-стирилзамещенных 1,8-нафталимида для применения в качестве флуоресцентных навигаторов в фотодинамической терапии онкологических заболеваний / М. А. Захарко, А. Н. Сергеева, П. А. Панченко, О. А. Федорова // Успехи в химии и химической технологии. — 2014. — Т. 28, № 10 (159). — С. 49–51.

Синтез и комплексообразование краунсодержащего полигетероциклического производного – мультипараметрического сенсора на катионы металлов / Ю. А. Глазова, Е. В. Луковская, Ю. В. Федоров и др. // Макрогетероциклы. — 2014. — Т. 7, № 4. — С. 373–379.

Синтез и комплексообразование хромофорного краунсодержащего стирилового производного тритиофена с катионами октан-1,8-диаммония. //Журнал органической химии / E. V. Lukovskaya, A. A. Kosmacheva, O. A. Fedorova и др. // Журнал органической химии. — 2014. — Т. 50, № 4. — С. 563–569.

ФОТОАКТИВНАЯ СУПРАМОЛЕКУЛЯРНАЯ СИСТЕМА НА ОСНОВЕ ФЛУОРЕСЦЕНТНОГО ПРОИЗВОДНОГО НАФТАЛИМИДА И ФОТОХРОМНОГО 18-КРАУН-6-ЭФИРСОДЕРЖАЩЕГО ПРОИЗВОДНОГО БЕНЗОПИРАНА / А. Н. Сергеева, П. А. Панченко, О. А. Федорова, Ю. В. Федоров // Успехи в химии и химической технологии. — 2014. — Т. 28, № 10. — С. 52–55.

ФОТОХИМИЧЕСКИЕ РЕАКЦИИ КРАУНСОДЕРЖАЩИХ СТИРИЛАЗИНОВ И ИХ КОМПЛЕКСОВ С КАТИОНАМИ МЕТАЛЛОВ / Т. М. Алиев, Д. В. Бердникова, Ю. В. Федоров, О. А. Федорова // Успехи в химии и химической технологии: сборник научных трудов. — Т. 28. — РХТУ им. Д.И. Менделеева Москва, 2014. — С. 60–63.

Berdnikova D. V., Fedorov Y. V., Fedorova O. A. Azadithiacrown ether based ditopic receptors capable of simultaneous multi-ionic recognition of ag+ and hg2+ // Dyes and Pigments. — 2013. — Vol. 96, no. 1. — P. 287–295. [ DOI ]

Comparative analysis of the pet and ict sensor properties of 1,8-naphthalimides containing aza-15-crown-5 ether moiety / P. A. Panchenko, Y. V. Fedorov, O. A. Fedorova, G. Jonusauskas // Dyes and Pigments. — 2013. — Vol. 98, no. 3. — P. 347–357. [ DOI ]

Effective stabilization of cis(-)isomer of styryl dye inside the cucurbit 7 uril cavity / E. Y. Chernikova, D. V. Berdnikova, Y. V. Fedorov, O. A. Fedorova // Макрогетероциклы. — 2013. — Vol. 6, no. 3. — P. 234–239. [ DOI ]

Metal-ion induced fret in macrocyclic dynamic tweezers / S. Delbaere, E. V. Tulyakova, E. Marmois et al. // Tetrahedron. — 2013. — Vol. 69, no. 38. — P. 8178–8185. [ DOI ]

Photoisomerization of crown-containing styrylbenzothiazole and styrylquinoline in complexes with hydroxypropyl-beta-cyclodextrin / S. V. Tkachenko, E. Y. Chernikova, E. N. Gulakova et al. // Protection of Metals and Physical Chemistry of Surfaces. — 2013. — Vol. 49, no. 2. — P. 181–188. [ DOI ]

Мутасова А. Д., Ощепков М. С., Федорова О. А. Азакраун-соединения и способы их получения // Успехи в химии и химической технологии. — 2013. — Т. 27, № 4. — С. 125–129.

Изучение комплексообразования бензоазакраун-лиганда с катионами иттрия, лютеция и лантана в водных растворах / Б. В. Егорова, М. С. Ощепков, Ю. В. Федоров и др. // Успехи в химии и химической технологии. — Т. 27. — РХТУ им. Д.И. Менделеева Москва, 2013. — С. 55–61.

Исследование комплексообразующих свойств бисстириловых красителей в присутствии молекул-хозяев: циклодекстрина и кукурбитурила / С. В. Ткаченко, М. С. Ощепков, О. И. Цветкова и др. // Успехи в химии и химической технологии. — 2013. — Т. 27, № 2. — С. 75–81.

Оптические свойства производных арилимидазофенантролина и их комплексов / Ю. А. Глазова, Е. В. Луковская, А. А. Бобылева и др. // Успехи в химии и химической технологии. — 2013. — № 2. — С. 82–88.

Разработка метода введения органических флуорофоров на основе 1,8- нафталимида в состав полимерных криогелей / М. В. Ощепкова, Е. М. Суханова, А. С. Ощепков и др. // Успехи в химии и химической технологии. — 2013. — Т. 27, № 3. — С. 127–131.

Синтез и комплексообразование бискраунированного тритиофена с виологенами / А. А. Космачева, Е. В. Луковская, О. А. Федорова и др. // Успехи в химии и химической технологии. — 2013. — Т. 27, № 2. — С. 89–93. Синтезирован 3,3’’-дизамещенный тритиофен с 18-краун-6 эфирными группами и изучено его комплексообразование с диаммонийными солями виологенов методами спектрофотометрического титрования, электрохимическими и ЯМР 1H. Показано, что краун-эфирные фрагменты в растворе ацетонитрила связывают катионы диаммония с образованием комплекса состава 1:1. На основании полученных данных предложена структура супрамолекулярного ансамбля.

Супрамолекулярные ансамбли краунсодержащих моно и бис(стирил)бипиридинов с катионами бария и железа(ii) / И. В. Сурикова, Н. Э. Шепель, О. А. Федорова и др. // Химическая технология. — 2013. — Т. 14, № 7. — С. 402–411. Изучено образование органо-металлических ансамблей на основе краунсодержащего моно(стирил)бипиридина с перхлоратами Ba(II) и Fe(II). Методами электронной спектроскопии, спектрофотометрического титрования, 1H NMR спектроскопии и ИЭР-масс спектрометрии определена структура, стехиометрия образующихся комплексов, а также рассчитаны их константы устойчивости.

Фотоиндуцированный перенос энергии в самоорганизующихся системах на основе стириловых красителей / А. Ю. Лебедева, Д. В. Бердникова, М. С. Ощепков и др. // Успехи в химии и химической технологии. — Т. 27. — РХТУ им. Д.И. Менделеева Москва, 2013. — С. 13–16.

Analysis of benzodiaza-15-crown-5 ether derivative binding properties by potentiometric and optical methods / O. Fedorova, Y. Fedorov, M. Oshchepkov, M. Dobrovolskaya // Journal of Physical Organic Chemistry. — 2012. — Vol. 25. — P. 835–839. [ DOI ]

Fedorova O., Fedorov Y., Oshchepkov M. Complexes of di- and triazacrown ethers with heavy metal ions in water solution // Electroanalysis. — 2012. — Vol. 8. — P. 1739–1744. [ DOI ]

Chernikova E. Y., Fedorov Y. V., Fedorova O. A. Cucurbituril as a new "host" of organic molecules in inclusion complexes // Russian Chemical Bulletin. — 2012. — Vol. 61, no. 7. — P. 1363–1390. [ DOI ]

Mono- and ditopic models of binding of a photochrome chromene annelated with an 18-crown-6 ether with protonated amino acids / P. Sergey, F. Yury, L. Vladimir et al. // Organic and Biomolecular Chemistry. — 2012. — Vol. 10. — P. 671–682. [ DOI ]

Photoinduced in situ generation of a dna-binding benzothiazoloquinolinium derivative / D. Berdnikova, O. Fedorova, E. Gulakova, H. Ihmels // Chemical Communications. — 2012. — no. 48. — P. 4603–4605. [ DOI ]

Polyclonal antibodies against human proteasome subunits psma3, psma5, and psmb5 / V. A. Livinskaya, V. A. Ivanov, O. A. Fedorova et al. // Hybridoma. — 2012. — Vol. 31, no. 4. — P. 272–278. A proteasome is a multi-subunit protein complex, which plays a central role in ubiquitin-dependent protein degradation in all eukaryotic cells. The 26S proteasome is composed of a catalytic 20S core complex and one or two 19S regulatory complexes. The 20S core complex forms a cylinder consisting of four stacked rings of seven α (PSMA1-7) or β (PSMB1-7) subunits. Target proteins are degraded in the cavity of the 20S complex due to proteolytic activities of three β subunits having catalytic sites located on the inner surface of the cylinder. The aim of this study was the generation of polyclonal antibodies against human proteasome subunits PSMA3, PSMA5, and PSMB5 and characterization of their experimental applications. To construct GST-fusion proteins, DNA sequences encoding PSMA3, PSMA5, and PSMB5 were cloned into prokaryotic expression vectors pGEX-5X-1 or pGEX-4T-3. Recombinant proteins GST-PSMA3, GST-PSMA5, and GST-PSMB5 were highly expressed in E. coli BL21 (DE3) cells, purified by glutathione-affinity chromatography and further used for rabbit immunization. The activity and specificity of the obtained antibody-containing sera were evaluated using Western blot analysis and immunoprecipitation. We have shown by Western blot analysis that our anti-PSMA3, anti-PSMA5, and anti-PSMB5 antibodies recognized both recombinant and endogenous proteins from different human cell lines. We have also shown that anti-PSMA3 and anti-PSMA5 sera were able to recognize and immunoprecipitate native forms of both endogenous and overexpressed FLAG-tagged proteins PSMA3 and PSMA5, respectively. Thus, the antibodies generated against PSMA3, PSMA5, and PSMB5 can be used in various experimental applications, including the evaluation of cellular levels of proteasome subunits in cell extracts and affinity purification of the endogenous and/or overexpressed proteasome subunits, which facilitates subsequent analysis of their post-translational modifications as well as protein-protein interactions in vivo. © 2012 Copyright, Mary Ann Liebert, Inc. [ DOI ]

Self-assembly of a ternary architecture driven by cooperative hg2+ ion binding between cucurbit[7]uril and crown ether macrocyclic hosts / E. Chernikova, D. Berdnikova, Y. Fedorov et al. // Chemical Communications. — 2012. — Vol. 48. — P. 7256–7258. [ DOI ]

Supramolecular control of photochemical and electrochemical properties of two oligothiophene derivatives at the air/water interface / S. Seleсtor, O. Fedorova, E. Lukovskaya et al. // Journal of Physical Chemistry B. — 2012. — Vol. 116, no. 5. — P. 1482–1490. [ DOI ]

Synthesis and sensor propeties of crown-containing derivatives of 4-(1,5-diphenyl-delta(2)-pyrazolin-3-yl)-1,8-naphthalimide / A. N. Sergeeva, P. A. Panchenko, Y. V. Fedorov, O. A. Fedorova // Protection of Metals and Physical Chemistry of Surfaces. — 2012. — Vol. 48, no. 5. — P. 524–533. [ DOI ]

Комплексообразование краунсодержащих полигетеро-циклических производных с перхлоратом магния / Ю. А. Глазова, Е. В. Луковская, А. А. Бобылева и др. // Успехи в химии и химической технологии. — 2012. — Т. 26, № 5. — С. 57–62.

Комплексообразование органического люминофора с тяжелыми металлами в монослоях Ленгмюра / Л. Б. Богданова, С. Л. Селектор, В. В. Арсланов и др. // "Структура и динамика молекулярных систем. Яльчик-2012". — Т. 2. — 2012. — С. 193–196.

Комплексообразование хромофорного краунсодержащего олиготиофена с катионом диаммония / А. А. Космачева, Е. В. Луковская, О. А. Федорова и др. // Успехи в химии и химической технологии. — 2012. — Т. 26, № 5. — С. 72–75.

Молекулярные структуры и кристаллические упаковки производных 2-стирилхиноксалина / Л. Г. КУЗЬМИНА, А. Г. СИТИН, Е. Н. ГУЛАКОВА и др. // Кристаллография. — 2012. — Т. 57, № 1. — С. 91–101. Определены кристаллическая и молекулярная структуры производных 2-стирилхиноксалина с различными заместителями в стириловом фрагменте. Степень планарности исследованных молекул варьирует в очень широких пределах – от 1.7o до 33.5o. В этиленовом фрагменте двойная связь существенно локализована. В кристаллах метокси- и оксиацетил- производных 2-стирилхиноксалина обнаружена “педальная” неупорядоченность этиленового фрагмента. Ни в одной из упаковок не обнаружено упаковочных мотивов, благоприятных для реакции фотоциклоприсоединения (ФЦП) с сохранением монокристалла. Кристаллические упаковки этих соединений и 2-(4-метилстирил)хиноксалина характеризуются стопочным мотивом типа “голова-к-голове”, который исключает возможность ФЦП с сохранением монокристалла, но не исключает такой реакции в поликристаллических пленках. Кристаллическая упаковка 2-(3,4-диметоксистирил)хиноксалина не содержит элементов со стэкинг-взаимодействиями. [ DOI ]

Синтез и фотохимические трансформации стириловых производных диазинов / Т. М. Алиев, Е. Н. Гулакова, Д. В. Бердникова и др. // Успехи в химии и химической технологии: сборник научных трудов. — Т. 24 из Международный конгресс молодых ученых. №8(137). — РХТУ им. Д.И. Менделеева Москва, 2012. — С. 101–105.

Трехкомпонентная фотоуправляемая система на основе краунсодержащего стирилбензотиазола и молекул-хозяев / С. В. Ткаченко, Е. Ю. Черникова, Е. Н. Гулакова и др. // Успехи в химии и химической технологии. — 2012. — Т. 26, № 5. — С. 106–110.

Complexes of amino acids with a crown-ether derivative of 4-styrylpyridine. monotopic or ditopic? / O. A. Fedorova, Y. V. Fedorov, I. E. Labazava et al. // Photochemical and Photobiological Sciences. — 2011. — Vol. 10, no. 12. — P. 1954–1962. [ DOI ]

Formation of complexes of 1,4-dioxa-7,10-dithiacyclododecane-8-carbonitrile with transition and heavy metal ions / L. G. Kuz'mina, E. V. Rakhmanov, A. A. Bobyleva, O. A. Fedorova // Russian Journal of General Chemistry. — 2011. — Vol. 81, no. 1. — P. 109–114. .

Hybrid sensor materials based on tin(iv) oxide and crown-containing 4-amino-1,8-naphthalimides / P. A. Panchenko, Y. V. Fedorov, O. A. Fedorova et al. // Mendeleev Communications. — 2011. — Vol. 21, no. 1. — P. 12–14. The cation-dependent spectral properties of crown-containing 4-aminonaphthalimide derivatives have been studied in an acetonitrile solution and within hybrid materials based on tin dioxide; these compounds can be of interest for producing fluorescent sensors for metal ions. [ DOI ]

Multimodal metal cation sensing with bis(macrocyclic) dye / T. Elena, D. Stephanie, F. Yuri et al. // Chemistry - A European Journal. — 2011. — Vol. 17. — P. 10752–10762. The synthesis, electrochemical, optical, and cation sensing properties of a bis(macrocyclic) dye 1, in which the benzo-15-crown-5 and phenylazathia- 15-crown-5 subunits are linked through a styryl pyridinium moiety, are reported. In this new ditopic receptor, the benzo-15-crown-5 macrocycle acts as a highly selective binding site for alkaline earth metal cations (MgII and BaII), whereas the phenylazathia- 15-crown-5 displays a strong binding affinity towards soft heavy-metal cations (HgII and AgI). The pronounced changes of the absorption and fluorescence spectra of this bichromophoric dye observed upon different metal cation addition make the dye suitable for dual-wavelength analysis and offer an enticing potential for multitasking sensors. [ DOI ]

Multimodal metal cation sensing with bis(macrocyclic) dye / E. Tulyakova, S. Delbaere, Y. Fedorov et al. // Chemistry - A European Journal. — 2011. — Vol. 17, no. 38. — P. 10752–10762. [ DOI ]

Self-organization of crown-containing hetarylphenylethenes, phthalic acid, and potassium cations into supramolecular assemblies / Y. V. Fedorov, E. Y. Chernikova, A. S. Peregudov et al. // Russian Chemical Bulletin. — 2011. — Vol. 60, no. 2. — P. 280–294. [ DOI ]

Исследование комплексообразования и фотохимической трансформации краунсодержащего стирилбензотиазола в присутствии 2-гидроксипропил-бета-циклодекстрина / С. В. Ткаченко, Е. Ю. Черникова, Е. Н. Гулакова и др. // Успехи в химии и химической технологии. — 2011. — Т. 25, № 4. — С. 34–38.

Исследование комплексообразования тиофенсодержащего 18-краун-6-эфира с ионами диаммония / Ж. С. Петрова, Е. В. Луковская, О. А. Федорова и др. // Успехи в химии и химической технологии. — 2011. — Т. 25, № 4. — С. 42–45. Одними из активно изучаемых краун-эфирных соединений в настоящее время являются краунированные тиофены и бензотиазолы. Краун-эфиры, обладающие ионофорными свойствами, способны значительно изменять электронные и оптические характеристики всей сопряженной системы, что дает возможность использовать их в качестве оптических сенсоров катионов металлов и ионов аммония. Последние предоставляют широкие возможности для тонкого управления строением и фотохимическими свойствами супрамолекул, поскольку ассортимент аммонийных соединений намного больше по сравнению с неорганическими субстратами.

КОМПЛЕКСООБРАЗОВАНИЕ КРАУНСОДЕРЖАЩЕГО МОНО(СТИРИЛ) ПРОИЗВОДНОГО БИПИРИДИНА С КАТИОНАМИ БАРИЯ И ЦИНКА / И. В. Сурикова, Н. Э. Шепель, О. А. Федорова, Ю. В. Фёдоров // Успехи в химии и химической технологии. — 2011. — Т. 25, № 4. — С. 25–30.

Молекулярные структуры и кристаллические упаковки 2-стирилхинолина и его производных / Л. Г. КУЗЬМИНА, А. Г. СИТИН, Е. Н. ГУЛАКОВА и др. // Кристаллография. — 2011. — Т. 56, № 4. — С. 663–673. [ DOI ]

НОВЫЕ СЕНСИБИЛИЗАТОРЫ ДЛЯ ФОТОДИНАМИЧЕСКОЙ ТЕРАПИИ РАКА НА ОСНОВЕ ПРОИЗВОДНЫХ НАФТАЛИМИДА И ПРИРОДНЫХ ХЛОРОФИЛЛОВ / А. Н. Сергеева, Р. И. Решетников, П. А. Панченко и др. // Успехи в химии и химической технологии. — 2011. — Т. 25, № 11. — С. 62–66.

Ощепков М. С., Федорова О. А. СЕНСОРЫ ДЛЯ БИОХИМИЧЕСКОГО АНАЛИЗА И МОНИТОРИНГА ОКРУЖАЮЩЕЙ СРЕДЫ // Успехи в химии и химической технологии. — 2011. — Т. 25. — С. 98–100.

СИНТЕЗ И СПЕКТРАЛЬНО-ЛЮМИНЕСЦЕНТНЫЕ СВОЙСТВА АЗАКРАУН-СОДЕРЖАЩИХНАФТАЛИМИДОВ И ИХ КОМПЛЕКСОВ С КАТИОНАМИ МЕТАЛЛОВ / А. С. Ощепков, М. С. Ощепков, П. А. Панченко и др. // Успехи в химии и химической технологии. — 2011. — Т. 25, № 4. — С. 69–74.

Синтез и сенсорные свойства краунсодержащих производных 4-пиразолинил-1,8-нафталимида / А. Н. Сергеева, П. А. Панченко, О. А. Федорова, Ю. В. Федоров // Успехи в химии и химической технологии. — 2011. — Т. 25, № 4. — С. 61–66.

Синтез фотохромных стирилзамещенных азинов / Е. Н. Гулакова, А. Г. Ситин, Л. Г. Кузьмина, О. А. Федорова // Журнал органической химии. — 2011. — Т. 47, № 2. — С. 253–260. [ DOI ]

A multiparametric sensor for cationic analysis / E. V. Lukovskaya, A. A. Bobyleva, A. A. Mizerev et al. // Russian Journal of Physical Chemistry A. — 2010. — Vol. 84, no. 12. — P. 2088–2091. [ DOI ]

Cation-dependent fluorescent properties of naphthalimide derivatives with n-benzocrown ether fragment / P. A. Panchenko, Y. V. Fedorov, V. P. Perevalov et al. // The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. — 2010. — Vol. 114, no. 12. — P. 4118–4122. [ DOI ]

Complex formation and photochemical properties of the crown- containing mono- and bis ( styryl ) bipyridine derivatives with transition metal cations / N. E. Shepel, O. A. Fedorova, E. N. Gulakova et al. // Макрогетероциклы. — 2010. — Vol. 3, no. 4. — P. 201–209. Complex formation of 15-crown-5 ether containing mono- and bis(styryl)bipyridine with transition metal perchlorates was studied. The complex stoichiometry, complex structure and stability constants were determined by electronic spectroscopy. The influence of metal ions on occurrence of E,Z-isomerization was analyzed; the optical characteristics of two isomers were calculated from the photolysis data. [ DOI ]

Metal ion modulated torsion angle in a ditopic oligothiophene ligand: Toward supramolecular control of π conjugation / L. Elena, F. Yuri, B. Alla et al. // Chemphyschem: a European journal of chemical physics and physical chemistry. — 2010. — Vol. 11. — P. 3152–3160. A π-conjugated oligomer bearing two 15-crown-5-containing styryl moieties connected at the inner β positions of the terminal thiophene nuclei can adopt either a U or a Z shape depending on the structures of its complexes with magnesium and barium ions. We show that barium cations lead to the formation of a mononuclear complex in solution, which causes the system to fold into the U shape. Magnesium ions lead to the same effect at low concentration, but force the ligand to adopt the Z-shaped geometry at high concentrations favoring formation of a binuclear complex. These geometrical reorganizations in solution are accompanied by profound changes in spectroscopic properties, which can be rationalized in terms of variations in the extent of electron delocalization along the oligothiophene backbone. The effects are analyzed by mass spectrometry and 1H NMR, UV/Vis absorption, and fluorescence spectroscopy in the steady-state and time-resolved regimes. The experimental results are compared to data calculated by using MOPAC2007 with the PM6 Hamiltonian including the COSMO solvation model. [ DOI ]

Metal ions drive thermodynamics and photochemistry of the bis(styryl) macrocyclic tweezer / E. V. Tulyakova, G. Vermeersch, E. N. Gulakova et al. // Chemistry - A European Journal. — 2010. — Vol. 16, no. 19. — P. 5661–5671. [ DOI ]

Structural and photochemical aspect of metal-ion-binding to a photochromic chromene annulated by crown-ether moiety / P. Sergey, D. Stéphanie, F. Olga et al. // Journal of Photochemistry and Photobiology A: Chemistry. — 2010. — Vol. 209. — P. 111–120. [ DOI ]

Synthesis and multiparameter sensor properties of the crown-containing thiophene derivatives / F. Olga, L. Elena, M. Artem et al. // Journal of Physical Organic Chemistry. — 2010. — Vol. 23, no. 3. — P. 246–254.

Synthesis and multiparameter sensor properties of the crown-containing thiophene derivatives / F. Olga, L. M. Elena, F. Yury et al. // Journal of Physical Organic Chemistry. — 2010. — Vol. 2010, no. 3. — P. 246–254. Novel ditopic receptor constructed as combination of bisthiophene with pyridinylvinyl and crown-containing styryl fragments was prepared. In the receptor pyridine residue is able to coordinate with Fe+2, Cd+2, Mg+2 metal cations whereas, the oxocrown ether moiety binds with alkaline earth metal (Mg+2, Ca+2 and Ba+2) cations. 1H NMR, optical, electrochemical, and ESI-MS results provided conclusive evidence of complex formation through the both coordination centers of molecule. The obtained results showed that cation complexation induced an optical and electrochemical changes particular for each binding centers. This type of multiparameter sensors has got interesting perspectives for a future design of a unique sensors promising for different analytical techniques.

Synthesis and multiparametric sensor properties of crown-containing thiophene derivatives / E. Lukovskaya, O. Fedorova, Y. Fedorov et al. // Journal of Physical Organic Chemistry. — 2010. — Vol. 23. — P. 246–254. A novel ditopic receptor was constructed as a combination of bisthiophene with pyridinylvinyl and crown-containing styryl fragments. In the receptor, the pyridine residue was able to coordinate Fe2+, Cd2+, and Mg2+ metal cations, whereas the oxocrown ether moiety bound with the alkaline earth metal (Mg2+, Ca2+, and Ba2+) cations. 1H NMR, optical, electrochemical, and ESI-MS results provided conclusive evidence of a complex formation through both the coordination centers of the molecule. The obtained results showed that cation complexation induces optical and electrochemical changes, particularly for each binding center. This type of multiparameter sensor provides interesting perspectives for the future design of unique sensors, promising different analytical techniques. Copyright © 2009 John Wiley & Sons, Ltd. [ DOI ]

Панченко П. А., Перевалов В. П., Федорова О. А. Дитиакраунсодержащие производные 4-ациламино-1,8-нафталимида в качестве флуоресцентных сенсоров на катионы металлов // Успехи в химии и химической технологии. — 2010. — Т. 24, № 2 (107). — С. 76–81. Спектрально-люминесцентные свойства производных 4-ацетиламинонафталимида, содержащих остаток бензодитиа-15-краун-5- и N-фенилазадитиа-15-краун-5-эфира в качестве N-арильного заместителя, изучены в ацетонитрильном растворе в присутствии и в от-сутствии катионов металлов. Показано, что связывание катионов ртути (II) указанными соединениями происходит селективно и сопровождается разгоранием флуоресценции. На основе азакраун-эфирного производного нафталимида получены полимерные сенсорные мембраны, способные детектировать катионы Аg+ и Hg2+ в водных растворах при концентрации порядка 10e-5 моль/л.

Ощепков М. С., Федорова О. А., Федоров Ю. В. ИССЛЕДОВАНИЕ КОМПЛЕКСООБРАЗОВАНИЯ ФОРМИЛЬНОГО ПРОИЗВОДНОГО n,n’-ДИМЕТИЛБЕНЗОДИАЗА-15-КРАУН-5 ЭФИРА С КАТИОНАМИ МЕТАЛЛОВ // Успехи в химии и химической технологии. — 2010. — Т. 24, № 6. — С. 32–36. В настоящей работе было синтезировано формильное производное бензодиаза- 15-краун-5-эфира, и исследовано комплексообразование полученного соединения с различными по природе катионами металлов в растворе ацетонитрила методами ЯМР-спектроскопии, и в воде с использованием метода потенциометрии.

Комплексообразование хромогенных бензо- и тиено-15-краун-5-эфиров с перхлоратами металлов / Ю. А. Глазова, Е. В. Луковская, А. А. Бобылева и др. // Успехи в химии и химической технологии. — 2010. — Т. 24, № 5. — С. 69–74. Синтезированы хромогенные бензо- и тиено-15-краун-5-эфиры с фрагментами бензотиазолия и изучено их комплексообразование с перхлоратом магния методом спектрофотометрического титрования. Показано, что краун-эфирный фрагмент изученных красителей способен в растворе ацетонитрила связывать катионы магния, что приводит к гипсохромным сдвигам спектров поглощения до 38 нм. Установлено, что замена бензокраун-эфирного фрагмента на тиенокраун-эфирный снижает комплексообразующую способность оптического комплексона.

Комплексообразующая способность замещенных оксатиакраун эфиров с вицинальным расположением атомов серы / Э. В. Рахманов, А. А. Бобылева, Е. В. Луковская и др. // Журнал общей химии. — 2010. — Т. 80, № 11. — С. 1860–1865.

Мультипараметрический сенсор для катионного катализа / Е. В. Луковская, А. А. Бобылева, А. А. Мизерев и др. // Журнал физической химии. — 2010. — Т. 84, № 12. — С. 1–5. Синтезирован краунсодержащий битиофен с Nметил4винилпиридиниевым и стирильным заме стителями, проявляющий свойства мультипараметрического сенсора, который можно использо вать при оптической и электрохимической детекции катионов щелочноземельных металлов.

Гулакова Е. Н., Колосова О. Ю., Федорова О. А. Получение новых функциональных производных 1,10-фенантролина // Известия АН СССР, Серия Химическая. — 2010. — С. 1263–1266. [ DOI ]

СИНТЕЗ, КОМПЛЕКСООБРАЗОВАНИЕ, ОПТИЧЕСКИЕ И ЭЛЕКТРОХИМИЧЕСКИЕ СВОЙСТВА ПРОИЗВОДНЫХ ОЛИГОТИОФЕНОВ / А. А. Мизерев, Е. В. Луковская, А. А. Бобылева и др. // Успехи в химии и химической технологии. — 2010. — Т. 24, № 5. — С. 89–95. Осуществлен синтез серии олиготиофенов, содержащих аннелированный краун- эфир. Методами спектрофотометрического титрования и циклической вольтамперометрии показано, что один из олиготиофенов является дитопным рецептором, обладающим оптическим и электрохимическим откликом на процесс комплексобразования.

Ферро-, пара- и термоиндуцированный магнетизм в фотомагнитных criii/mnii / C. М. Алдошин, Н. А. Санина, Р. Б. Моргунов и др. // Известия Академии наук. Серия химическая. — 2010. — № 3. — С. 487–495. Разделены экспериментально ферро-, пара- и термоиндуцированный магнетизм в фотомагнитных CrIII/MnII.

Cucurbit 7 uril complexes of crown-ether derived styryl and (bis)styryl dyes / O. A. Fedorova, E. Y. Chernikova, Y. V. Fedorov et al. // Journal of Physical Chemistry B. — 2009. — Vol. 113, no. 30. — P. 10149–10158. [ DOI ]

Novel crown-containing 3-styryl derivatives of oligothiophenes: synthesis, structure, and optical and electrochemical characteristics / E. V. Lukovskaya, A. A. Bobyleva, O. A. Fedorova et al. // Russian Chemical Bulletin. — 2009. — Vol. 58, no. 7. — P. 1509–1515. [ DOI ]

Synthesis and spectral properties of 4-amino- and 4-acetylamino-n-arylnaphthalimides containing electron-donating groups in the n-aryl substituent / P. A. Panchenko, Y. V. Fedorov, O. A. Fedorova et al. // Russian Chemical Bulletin. — 2009. — Vol. 58, no. 6. — P. 1233–1240. [ DOI ]

The complex formation properties of 18-crown-6-2-styrylbenzothiazole and the product of its photocyclization / O. A. Fedorova, E. N. Gulakova, I. E. Lobazova et al. // Russian Journal of Physical Chemistry A. — 2009. — Vol. 83, no. 6. — P. 1039–1043. [ DOI ]

Фёдорова О. А., Ощепков М. С. ИЗУЧЕНИЕ УСЛОВИЙ И МЕХАНИЗМА ОБРАЗОВАНИЯ АЗАКРАУН-СОЕДИНЕНИЙ РАЗЛИЧНОГО СТРОЕНИЯ // Успехи в химии и химической технологии. — 2009. — Т. 23. — С. 33–37.

Новые краунсодержащие 3-стирилзамещенные олиготиофены: синтез, строение, оптические и электрохимические характеристики / Е. В. Луковская, А. А. Бобылева, О. А. Федорова и др. // Известия АН СССР, Серия Химическая. — 2009. — № 7. — С. 1465–1470. Предложен метод синтеза 3-замещенных политиофеновых производных, имеющих в своем составе два краунсодержащих стириловых фрагмента. Показано, что оптические свойства полученных соединений характеризуются наличием интенсивных полос поглощения и флуоресценции. Процессы окисления в производных тиофенов протекают с включением краунсодержащего стирилового фрагмента и должны быть чувствительны к присутствию катиона металла в краун-эфирной полости.

2+2 -photocycloaddition reaction of self-assembled crown-containing 2-styrylpyridinium perchlorate in a solid state / E. V. Tulyakova, O. A. Fedorova, Y. V. Fedorov, A. V. Anisimov // Journal of Photochemistry and Photobiology A: Chemistry. — 2008. — Vol. 200, no. 1. — P. 90–95. [ DOI ]

A photochemical electrocyclization of the benzothiazolylphenylethenes involving a cn bond formation / O. A. Fedorova, E. N. Gulakova, Y. V. Fedorov et al. // Journal of Photochemistry and Photobiology A: Chemistry. — 2008. — Vol. 196, no. 2. — P. 239–245. [ DOI ]

Specific features of reversible e-z-photoisomerization of crown-containing 4-styrylpyridine complexes with various cations / Y. V. Fedorov, N. E. Shepel, E. Y. Chernikova et al. // Russian Chemical Bulletin. — 2008. — Vol. 57, no. 11. — P. 2385–2393. [ DOI ]

Spectroscopic study of mono- and bis(styryl) dyes of the pyridinium series containing azathiacrown ether residue / E. V. Tulyakova, O. A. Fedorova, Y. V. Fedorov et al. // Journal of Physical Organic Chemistry. — 2008. — Vol. 21. — P. 372–380. [ DOI ]

Монослои и пленки Ленгмюра-Блоджетт краунированных олиготиофенов. Влияние структуры на оптические свойства / С. Л. Селектор, Н. А. Тарасова, О. А. Федорова и др. // Сборник статей XV Всероссийской конференции Структура и динамика молекулярных систем. — Т. 15. — Издательство МарГТУ Йошкар-Ола, 2008. — С. 281–285.

Effect of arrangement of the styryl fragment on the optical properties and complexation of mono-and bis(styryl)-substituted n-methylpyridinium perchlorates containing benzo-15-crown-5 ether moieties / E. V. Tulyakova, O. A. Fedorova, Y. V. Fedorov et al. // Russian Chemical Bulletin. — 2007. — Vol. 56, no. 11. — P. 2166–2174. [ DOI ]

Investigation of crown-containing styryilthiophene derivatives which are optically and electrochemically sensitive to the presence of metal cations / E. V. Lukovskaya, A. A. Bobylyova, O. A. Fedorova et al. // Synthetic Metals. — 2007. — Vol. 157, no. 22-23. — P. 885–893. The analysis of complex formation of crown-containing styryl and bisstyryl thiophene derivatives with alkaline earth metal cations and the investigation of optical and electrochemical responses induced by metal cations are reported. The monostyryl derivative forms weakly fluorescent inclusion complexes with Mg2+ cations and weakly fluorescent anti-sandwich complex with Ba2+ cations. In case of bisstyryl thiophene compounds the Mg2+ complexes are fluorescent, whereas, the sandwich complex with composition (1b)2·(Ba2+)2 or (1b)2·(Ba2+)3 are weakly fluorescent. The results of the investigations showed that the crown-containing mono- and bisstyryl thiophene derivatives are optically and electrochemically sensitive to the presence of metal cations.

Spironaphtoxazines produced from crown-containing dihydroisoquinolines: Synthesis and spectroscopic study of cation-dependent photochromism / V. V. Korolev, D. Y. Vorobyev, E. M. Glebov et al. // Journal of Photochemistry and Photobiology A: Chemistry. — 2007. — Vol. 192, no. 2-3. — P. 75–83. Synthesis and photochromic properties of a novel spironaphtoxazine (SNO) obtained from a crown-containing dihydroisoquinoline are described. The comparison of spectral and kinetic properties with that of a crown free SNO is performed. For a crown-containing SNO, the complex formation with alkaline earth metal cations occurs both for spiro (S) and merocyanine (M) forms of the molecule. For the cations of large size (for instance, Ba2+) the formation of sandwich complex was found. For a crown free SNO, only Worm complex with metal cation is possible. In all cases, the complex formation affects both on the position of the M-form absorption maximum and the M-form characteristic lifetime. (c) 2007 Elsevier B.V All rights reserved. [ DOI ]

Supramolecular photochemical synthesis of an unsymmetrical cyclobutane / O. Fedorova, Y. V. Fedorov, E. Gulakova et al. // Photochemical and Photobiological Sciences. — 2007. — Vol. 6, no. 10. — P. 1097–1105. [ DOI ]

Synthesis, complexation, and e-z photoisomerization of azadithiacrown-containing styryl dyes as new optical sensors for mercury cations / E. V. Tulyakova, O. A. Fedorova, Y. V. Fedorov et al. // Russian Chemical Bulletin. — 2007. — Vol. 56, no. 3. — P. 513–526. [ DOI ]

Synthesis, structures, and optical and electrochemical characteristics of novel crown-containing polythiophene systems / E. V. Lukovskaya, A. A. Bobylyova, O. A. Fedorova et al. // Russian Chemical Bulletin. — 2007. — Vol. 56, no. 5. — P. 967–974. [ DOI ]

Синтез строение, оптические и электрохимические характеристики новых краунсодержащих политиофеновых систем / Е. В. Луковская, А. А. Бобылева, О. А. Федорова и др. // Известия АН СССР, Серия Химическая. — 2007. — № 5. — С. 932–939. В настоящем исследовании описан синтез, строение, оптические и электрохимические характеристики неизвестных ранее краунсодержащих стирилзамещенных моно- и политиофеновых производных. Для получения стирилзамещенных тиофенов был использован метод Виттига-Хорнера, политиофены получали по методам Сузуки и Стилле. Исследования оптических характеристик полученных соединений показали, что краун-содержащие политиофены обладают интенсивными спектрами поглощения и флуоресценции, расположение и форма полос поглощения и эмиссии которых зависит от структуры соединения.

A facile transformation of the hydroxy substituted oxathiacrown ethers journal: Synthetic communications / E. V. Tulyakova, E. V. Rakhmanov, E. V. Lukovskaya et al. // Synthetic Communications. — 2006. — Vol. 36, no. 16. — P. 2329–2336.

Crystal and molecular structure of a series of 15-crown-5-containing styryl heterocycles and their dimethoxy substituted analogues / L. G. Kuz'mina, O. A. Fedorova, E. N. Andryukhina et al. // Crystallography Reports. — 2006. — Vol. 51, no. 3. — P. 434–447. A comparative study of the molecular geometry and crystal packing of crown-containing styryl heterocycles and their dimethoxy substituted analogues is performed. It is established that all the compounds exhibit an identical type of distortions of the geometry of the central styryl fragment. These are the localization of the pi-electron density at the ethylene bond and the bond alternation in a half of the phenyl ring due to the conjugation of lone electron pairs of the oxygen substituents with the chromophore system of the molecule. A comparative analysis of the crystal packings of the compounds reveals extended separate hydrophilic and hydrophobic regions. The hydrophilic regions are built of crown ether fragments, and the hydrophobic regions consist of pi-conjugated and aromatic molecular fragments. The hydrophobic regions are characterized by a wide variety of packing motifs, among which stacking packing is absent. For two compounds, the formation of sandwich dimers that are preorganized to enter into the photochemical [2 + 2]cycloaddition reaction is observed. [ DOI ]

Earliest changes in the left ventricular transcriptome postmyocardial infarction /  Harpster, H. M,  Bandyopadhyay et al. // Mammalian Genome. — 2006. — Vol. 17. — P. 701–715.

Stilbene analogs in hula-twist photoisomerization / Y. Lan-Ying, H. Miki, I. Yasushi et al. // Photochemical and Photobiological Sciences. — 2006. — Vol. 5. — P. 874–882. [ DOI ]

Supramolecular assemblies of crown-containing 2-styrylbenzothiazole with amino acids / O. A. Fedorova, E. N. Andryukhina, Y. V. Fedorov et al. // Organic and Biomolecular Chemistry. — 2006. — Vol. 4, no. 6. — P. 1007–1013. [ DOI ]

Synthesis and cation-dependent photochromism of spironaphthoxazines obtained from crown-containing dihydroisoquinolines / V. V. Korolev, D. Y. Vorobyev, E. M. Glebov et al. // Mendeleev Communications. — 2006. — no. 6. — P. 302–304. The formation of complexes between spirooxazines (SNOs) containing crown-ether and dihydroquinoline moieties and alkaline earth metal ions affects the spectral and kinetic properties of the SNO open form. [ DOI ]

Synthesis and complexation properties of photochromic benzochromenes containing aza- and diaza-18-crown-6-ether fragments / O. A. Fedorova, Y. P. Strokach, A. V. Chebun'kova et al. // Russian Chemical Bulletin. — 2006. — Vol. 55, no. 2. — P. 287–294. Complex formation of Mg2+, Ba2+, and Pb2+ perchlorates with 3,3-diphenyl-3H-benzo[f]chromenes containing aza- and diaza-18-crown-6-ether or morpholine fragments was studied. The strong influence of the metal cations on the spectral characteristics of these organic ligands and on the kinetic of photochromic transformations was found. The results obtained were explained by the formation of carbonyl-"capped" complexes of various structures. [ DOI ]

Synthesis, complex-formation, and extracting ability of new derivatives of dithia-13(16)-crown-4(5) ethers / E. V. Tulyakova, E. V. Rakhmanov, E. V. Lukovskaya et al. // Chemistry of Heterocyclic Compounds. — 2006. — Vol. 42, no. 2. — P. 206–215. Various methods of synthesizing functional derivatives of dithia-13(16)-crown-4(5) ethers are proposed. Complex-formation of the obtained compounds with Ag+ and Pb2+ ions has been studied using 1H NMR. A radiometric method was used to investigate the extracting ability of substituted dithia-13(16)-crown-4(5) ethers in relation to Ag+ and Cd2+ ions from aqueous solution in the presence of anions of various degree of hardness, with determination of the metal content. [ DOI ]

The photochemistry of a bis-crown ether based on benzobis(thiazole) and its alkaline earth metal cation complexes / Y. V. Fedorov, O. A. Fedorova, N. E. Schepel et al. // Photochemistry and Photobiology. — 2006. — Vol. 82, no. 4. — P. 1108–1115. Irradiation of acetonitrile solutions of the bis-crown ether E,E-2,7-bis[2-(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxabenzocyclopentadecen-2-yl)vinyl]-benzo[1,2-d;3,4-d’]bisthiazole (hereafter, 1) gives efficient E –> Z photoisomerization (initial phi(trans –> cis) = 0.48), leading to lambda(exc)-dependent quasi-photostationary states composed primarily of E,Z and E,E isomer mixtures. Further irradiation gives [2 + 2]-cycloadducts of 1. In the presence of Ba2+ ions, essentially quantitative formation of 2:2 complexes, 1(2) x (Ba2+)2 controls the photochemical outcome. E –> Z photoisomerization of the ligand is entirely suppressed and efficient intramolecular [2 + 2]-photocycloaddition in the complexes leads to cyclobutane dimers of 1 (phiCB = 0.26). The reactivity of 1 in the presence of Mg2+ ions for which 1:2 complex formation dominates gives both cis-trans photoisomerization and enhanced photocycloaddition. [ DOI ]

Синтез, комплексообразование, и экстракционная способность новых производных дитиа-13(16)-краун-4(5)-эфиров / Е. В. Тулякова, Э. В. Рахманов, Е. В. Луковская и др. // Химия гетероциклических соединений. — 2006. — № 2. — С. 233–243.

Electrocyclic reaction of crown-containing 2-styrylbenzothiazoles / E. N. Andryukhina, O. A. Fedorova, Y. V. Fedorov et al. // Russian Chemical Bulletin. — 2005. — Vol. 54, no. 5. — P. 1328–1330. The photoinduced electrocyclic transformation of 15-crown-5-containing 2-styrylbenzothiazoles into condensed benzothiazoloquinoline derivatives was discovered. The process is accompanied by the formation of a C-N bond and elimination of a hydrogen atom. [ DOI ]

Facile synthesis of novel styryl ligands containing a 15-crown-5 ether moiety / O. A. Fedorova, E. N. Andryukhina, M. M. Mashura, S. P. Gromov // ARKIVOC. — 2005. — P. 12–24. Novel ligands containing a 15- crown- 5 ether moiety and six- membered heterocyclic residues with different combinations of N atoms were prepared by condensation of methyl- substituted six- membered heterocyclic bases with 4'- formylbenzo- 15- crown- 5 ether; the best results were obtained in the presence of tBuOK in DMF. For dimethyl- substituted heterocyclic bases as the initial heterocyclic components, the competition of mono- and bis- condensation reactions is analyzed. The role of complex formation in the syntheses is discussed.

Investigation of the azacrown-ether substituted naphtopyranes / A. V. Chebun'kova, S. P. Gromov, Y. P. Strokach et al. // Molecular Crystals and Liquid Crystals. — 2005. — Vol. 430. — P. 67–73. The study of the complexation of 3,3-diphenyl-3H-benzo[f]chromenes containing an aza-15-crown-5-ether or morpholine units with Mg2+, Ba2+ and pb(2+) in acetonitrile are reported. The spectroscopic and kinetic behaviour of the photomerocyanine isomers of these chromenes is strongly affected by complexation with metal cations. In order to interpret the experimental data, a formation of anion-"capped" complexes was supposed. [ DOI ]

One-pot synthesis of 6'-amino-substituted spirooxazines / A. V. Koshkin, V. Lokshin, A. Samat et al. // SYNTHESIS-STUTTGART. — 2005. — no. 11. — P. 1876–1880. A one-pot synthesis of 6'-amino-substituted spiroindolinonaphth[2, 1-b][1, 4]oxazines is developed through the condensation of 2-methylene-1,3,3-trimethylindoline derivatives and 1-amino-2-naphthol in the presence of different secondary amines and oxidizing agents using methanol or toluene as the solvent. The main advantage of the method is its simplicity, and starting from readily accessible reagents. it allows the preparation of amino derivatives of spironaphthoxazine with good yields under mild reaction conditions.

Self-assembly of a (benzothiazolyl)ethenylbenzocrown ether into a sandwich complex and stereoselective [2+2] photocycloaddition / S. P. Gromov, A. I. Vedernikov, Y. V. Fedorov et al. // Russian Chemical Bulletin. — 2005. — Vol. 54, no. 7. — P. 1569–1579. In the presence of Ba2+ ions, (benzothiazolyl)ethenylbenzocrown ether forms the stable sandwich complex 2L center dot Ba2+ with an unusual structure, in which the benzothiazole fragments are arranged one above the other. Irradiation of the sandwich complex with visible light induces stereoselective [2+2] cycloaddition giving rise to two "head-to-head" isomers of biscrown-cyclobutane. The addition of dibasic dicarboxylic acids that additionally stabilize the sandwich complex in a favorable conformation affects the isomer ratio of the cyclobutanes formed. The conformational equilibria for the sandwich complex and cyclobutanes were studied by H-1 N MR spectroscopy. [ DOI ]

Supramolecular assemblies of crown-containing 4-styrylpyridine in the presence of metal cations / Y. V. Fedorov, O. A. Fedorova, E. N. Andryukhina et al. // Journal of Physical Organic Chemistry. — 2005. — Vol. 18, no. 10. — P. 1032–1041. Optical and x-ray experiments showed the possibility of studying 4-styrylpyridine with a 15-crown-5 ether fragment to bind metal cations through the participation of two centres: the crown ether moiety and the heterocyclic part. The metal cations studied can be divided into three groups. Alkaline earth metal cations form complexes with the crown ether centre, H+, Co2+ and Cd2+ prefer coordination with the N-atom of heterocyclic part and Hg2+ cations form complexes through coordination with both binding centres. Copyright (c) 2005 John Wiley & Sons, Ltd. [ DOI ]

Synthesis and multitopic complex formation of a photochromic bis(crown ether) based on benzobis(thiazole) / Y. V. Fedorov, O. Fedorova, N. Schepel et al. // The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. — 2005. — Vol. 109, no. 38. — P. 8653–8660. [ DOI ]

Synthesis and structures of azine-based crown-containing hetarylpenylethenes / E. N. Andryukhina, Y. Mashura, O. A. Fedorova et al. // Russian Chemical Bulletin. — 2005. — Vol. 54, no. 7. — P. 1700–1709. Condensation of methyl-substituted six-membered heteroaromatics containing one or two nitrogen atoms with aldehyde derived from benzo-15-crown-5 ether in DMF in the presence of (BuOK)-O-t afforded 15-crown-5-containing hetarylphenylethenes. According to the results of NMR spectroscopy, these compounds exist as mixtures of syn and anti conformers in solution (MeCN-d3). The structures of two compounds were established by X-ray diffraction analysis. [ DOI ]

Synthesis, complexation, and photochemistry of benzobisthiazole-based bis(crown ether) / Y. V. Fedorov, O. A. Fedorova, N. E. Shepel et al. // Russian Chemical Bulletin. — 2005. — Vol. 54, no. 9. — P. 2119–2128. Benzobisthiazole-based bis(crown ether) was synthesized and its complexation with alkali and alkaline earth cations was studied. Photochemical transformations of the free ligand and its complexes with alkaline earth cations involve E,Z-photoisomerization and [2+2] photocycloaddition. [ DOI ]

Transformation of 6'-aminosubstituted spironaphthoxazines induced by pb(ii) and eu(iii) cations / O. A. Fedorova, A. V. Koshkin, S. P. Gromov et al. // Journal of Physical Organic Chemistry. — 2005. — Vol. 18, no. 6. — P. 504–512. The transformation of spiroindolinonaphth[2,1-b][1,4]oxazines (SNOs) conjugated with aza-15(18)crown-5(6) ether moieties or morpholine in the presence of Pb2+ or lanthanoid cations in MeCN solution was studied by UV-Vis, NMR and surface-enhanced resonance Raman scattering spectroscopy methods. The Pb2+ or EU3+ cations induce the formation of the betaine merocyanine form of SNO. When the merocyanine complexes are kept in the dark, the corresponding oxazole derivatives are formed irreversibly and regioselectively. Copyright (c) 2005 John Wiley & Sons, Ltd. [ DOI ]

Синтез, комплексообразование и фотохимия бис(краун эфира) на основе бензобистиазола / Ю. В. Федоров, О. А. Федорова, Н. Э. Шепель и др. // Известия Академии наук. Серия химическая. — 2005. — № 9. — С. 2056–2065. Синтезирован бис(краун-эфир) на основе бензобистиазола, изучено его комплексо-образование с катионами щелочных и щелочноземельных металлов. Фотохимические превращения свободного лиганда и его комплексов с катионами щелочноземельных металлов включают E,Z-фотоизомеризацию и [2+2]-фотоциклоприсоединение.

Guest-host interactions between crown-containing 2-styrylbenzothiazole and hp-beta-cd / Y. V. Fedorov, O. A. Fedorova, E. N. Andryukhina et al. // JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY. — 2004. — Vol. 49, no. 3-4. — P. 283–289. The inclusion complexes of the trans-isomer of 2-[2-(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxabenzocyclopentadecen-2-yl)- vinyl]- benzothiazole (CSB) with 2-hydroxypropyl-beta-cyclodextrin (HP-beta-CD) were investigated by electronic absorption and fluorescence spectroscopies in aqueous solution. The addition of HP-beta-CD has very little effect on the absorption spectra of CSB. A 17-nm blue shift and pronounced fluorescence enhancements in the emission spectrum of CSB were observed. 1: 1 and 1: 2 stoichiometries were found for complexes of CSB with HP-beta-CD, and formation constants of the complexes and other thermodynamic parameters were estimated from fluorescence measurements. In the case of the 1: 1 CSB: HP-beta-CD complex, the formation constant was equal to 3,802 at 293 K, the complexation reaction was exothermic (DeltaH(0) = - 9.2 +/- 1.1 kJ mol(-1)) and presented a positive entropy value (DeltaS(0) = 37.3 +/- 3.8 J mol(-1) K-1). A molecular structure was proposed for the CSB: HP-beta-CD inclusion complex. [ DOI ]

Microwave-assisted solvent-free synthesis of the substituted spiroindolinonaphth[2,1-b][1,4]oxazines / A. V. Koshkin, O. A. Fedorova, V. Lokshin et al. // Synthetic Communications. — 2004. — Vol. 34, no. 2. — P. 315–322. The synthesis of the substituted spiroindolinonaphth[2,1-b][1,4]oxazines 3a-e is developed through the condensation of 2-methylene-1,3,3-trimethylindoline derivatives and 1-nitroso-2-naphthol under microwave irradiation. In the same conditions, in presence of morpholine the 6'-morpholinosubstituted compounds 4a, b, d, e are formed. The main advantages of the method are the short reaction time, solvent-free reaction condition, cleaner reaction products and the higher product yields in comparison with known methods of synthesis. [ DOI ]

Synthesis of oxathiacrown ethers - new hosts for transition and heavy metals and study of their fluorscent and extraction properties. part i / E. V. Tulyakova, E. V. Rakhmanov, A. A. Bobylyova et al. // Chemicke Listy. — 2004. — Vol. 98. — P. 51–52.

Synthesis of formyl derivatives of benzodiazacrown ethers and benzoeryptands / O. A. Fedorova, A. I. Vedernikov, I. E. Baronova et al. // Russian Chemical Bulletin. — 2004. — Vol. 53, no. 2. — P. 396–403. A simple and convenient procedure was developed for the synthesis of formyl derivatives of benzodiazacrown ethers and benzocryptands by condensation of 3,4-bis(2-iodoethoxy)benzaldehyde with alpha,omega-oligoomalkanediamines or diazacrown ethers in the presence of alkali metal carbonates under high-dilution conditions in various organic solvents and their mixtures with water. In the reactions giving rise to diazacrown ethers, alkali metal cations exhibit the negative template effect resulting in a decrease in the yield of the target product if the size of the cation matches well the size of the cavity of the crown ether formed. All N,N'-bis(carboxymethyl) derivative was prepared from the formyl derivative of benzodiaza-18-crown-6. [ DOI ]

Antimutagenic and antioxidant activities of crown compounds in comparison with the effects of garlic extract / G. D. Zasukhina, I. M. Vasil'eva, E. S. Mikhal'chik et al. // Bulletin of Experimental Biology and Medicine. — 2003. — Vol. 135, no. 3. — P. 261–264. Antimutagenic activity of N-carboxyalkyl derivatives of aza- and benzoazacrown compounds was revealed and antimutagenic activity of garlic extract was confirmed. Specific genoprotective effect of crown compounds towards the effects of various mutagens was demonstrated. The antimutagenic effect of these compounds was not realized via antioxidant mechanisms, while the protective effect of garlic extract was associated with its antioxidant and reparative activities. [ DOI ]

Cation-dependent photochromic properties of novel ditopic receptors / O. A. Fedorova, Y. V. Fedorov, E. N. Andrjukhina et al. // Pure and Applied Chemistry. — 2003. — Vol. 75, no. 8. — P. 1077–1084. Novel crown-containing 2-styrylbenzothiazoles were prepared to obtain optical ditopic receptors that can bind alkaline-earth metal cations by a crown ether fragment and could serve as host for the heavy metal cations and proton owing to the presence of the heterocyclic part. Photochemical transformations of the ditopic receptors depend on the type of metal cations present in solution. They include trans-cis-isomerization, [2+2]-cycloaddition, and electrocyclic reaction. [ DOI ]

Complex formation of 2,2-diphenyl-2h-benzo[f]chromene containing the aza-18-crown-6-ether fragment in the polymeric layer / V. B. Nazarov, O. A. Fedorova, S. B. Brichkin et al. // Russian Chemical Bulletin. — 2003. — Vol. 52, no. 12. — P. 2661–2667. The synthesis of 2,2-diphenyl-2H-benzo[f]chromene containing the aza-18-crown-6-ether fragment was described. Its complex formation with alkaline-earth metal ions in dibutyl phthalate and the polymeric gelatin film was investigated. The treatment of the layers containing the ionophore mentioned with aqueous solutions of the corresponding salts in the presence of NaBPh4 as the phase transfer catalyst results in the extraction of the metal cation into the polymeric layer due to complex formation with crown-containing benzo[f]chromene. The complex formation is accompanied by changes in the spectroscopic characteristics of chromene in the closed and open forms and an increase in the lifetime of the merocyanine form. The effects obtained depend on the metal cation concentration in a solution and the time of layer treatment. [ DOI ]

Ditopic complex formation of the crown-containing 2-styrylbenzothiazole / Y. V. Fedorov, O. A. Fedorova, E. N. Andryukhina et al. // New Journal of Chemistry. — 2003. — Vol. 27, no. 2. — P. 280–288. The complex formation of 2-styrylbenzothiazole containing a 15-crown-5 ether fragment with alkaline earth metal cations, proton, Ag+ and Hg2+ was studied by optical and X-ray diffraction methods. The compound is able to bind the metal cations through the participation of two centers: the crown ether moiety and the heterocyclic part. The alkaline earth metal cations form complexes with the macrocyclic part of the molecule. The formation of a strong sandwich complex was found in the case of Ba2+. The proton coordinates with the N atom of the heterocyclic fragment of the molecule. The Ag+ and Hg2+ cations bind with both centers of the molecule: the crown ether fragment and the heterocyclic residue. [ DOI ]

Fedorova O. A., Andryukhina E. N., Gromov S. P. Facile synthesis of novel 2-styrylbenzothiazoles containing crown ether moieties // SYNTHESIS-STUTTGART. — 2003. — no. 3. — P. 371–374. Novel 2-styrylbenzothiazoles containing crown ether moieties with different combinations of 0, S, and N atoms were prepared by condensation of 2-methylbenzothiazole with formyl derivatives of benzocrown ethers in the presence of alkali metal alkoxides or by Wittig reaction. The role of complex formation in these syntheses is discussed.

Novel photoswitchable receptors: Synthesis and cation-induced self-assembly into dimeric complexes leading to stereospecific [2+ 2]-photocycloaddition of styryl dyes containing a 15-crown-5 ether unit / S. P. Gromov, E. N. Ushakov, O. A. Fedorova et al. // Journal of Organic Chemistry. — 2003. — Vol. 68, no. 16. — P. 6115–6125. Styryl dyes 4a−e containing a 15-crown-5 ether unit and a quinoline residue with a sulfonatoalkyl or sulfonatobenzyl N-substituent were synthesized. The relationship between the photochemical behavior of these dyes and their aggregates derived from complexation with Mg2+ in MeCN was studied using 1H NMR and absorption spectroscopy. The E-isomers of 4a−e were shown to form highly stable dimeric (2:2) complexes with Mg2+. Upon irradiation with visible light, the dimeric complexes undergo two competing photoreactions, viz., geometric E → Z isomerization, resulting in an anion-capped 1:1 complex of the Z-isomer with Mg2+ and stereospecific syn-head-to-tail [2+2]-cycloaddition, affording a single isomer of bis-crown-containing cyclobutane. The N-substituent in the dye has a dramatic effect on the photochemical behavior of the dimeric complex. Molecular dynamics and semiempirical quantum-chemical calculations were carried out to interpret the observed photocycloaddition in the dimer. Conformational equilibria for the dimer of (E)-4b were analyzed using 1H NMR spectroscopy. [ DOI ]

Photochemical electrocyclization of the indolinylphenylethenes involving a c-n bond formation / O. A. Fedorova, Y. V. Fedorov, E. N. Andryukhina et al. // Organic Letters. — 2003. — Vol. 5, no. 24. — P. 4533–4535. A novel oxidative photodehydrocyclization of indolinylphenylethenes to a polycyclic heteroaromatic cation with good yields was described. Starting from the trans derivative, the phototransformation is a multistep process. The process includes two photochemical reactions and a trans-cis isomerization reaction, followed by an 1-aza-1,3,5-hexatrienic electrocyclic reaction involving the formation of a C-N bond. The cyclized product gives the stable heteroaromatic cations from hydride elimination with oxygen from air or iodine. [ DOI ]

Photocontrol of ca2+ complexation with an azacrown-containing benzochromene / E. N. Ushakov, V. B. Nazarov, O. A. Fedorova et al. // Journal of Physical Organic Chemistry. — 2003. — Vol. 16, no. 5. — P. 306–309. The new azacrown-containing benzochromene 1a was synthesized in order to study the effect of its reversible photochromic reaction on complex formation with Ca2+ in acetonitrile. It was found that both the initial chromene la and its photoinduced merocyanine isomer 2a are able to form 1:1 complexes with Ca2+, in which the metal cation coordinates to the crown ether moiety. The complexation causes strong spectroscopic shifts and leads to an increase in the dark lifetime of 2a. The equilibrium constant for the 1: 1 complexation decreases upon photoinduced ring-opening reaction (log K = 4.9 and 4.1 for 1a and 2a, respectively). Copyright (C) 2003 John Wiley Sons, Ltd. [ DOI ]

Alfimov M. V., Fedorova O. A., Gromov S. P. Photoswitchable molecular receptors // Journal of Photochemistry and Photobiology A: Chemistry. — 2003. — Vol. 158, no. 2-3. — P. 183–198. The review describes photoswitchable molecular receptors based on crown-ether systems. The important feature of the systems is reversible change in the capacity of a photochromic host molecule for association with guests upon irradiation. From the other side, the exploration of the complex formation process in crown-ether systems leads to a novel approach to the modification of photochromic behavior. The results obtained show that the introduction of crown-ether moieties into dye molecules affords compounds that can change their spectral and photochromic properties upon complex formation. The researchers believe that the novel photochromic systems can now be regarded as being promising for traditional applications (photochromic ophthalmic lenses or camera filters, reversible holographic systems and cosmetics) and molecular electronics, biomimetic chemistry, and optical information storage. (C) 2003 Elsevier Science B.V All rights reserved. [ DOI ]

Study of properties of polymolecular layers of crown-containing indoline spironaphthooxazines / L. V. Stebunova, I. A. Nagovitsyn, G. K. Chudinova et al. // Zhurnal Nauchnoi I Prikladnoi Fotografii. — 2003. — Vol. 48, no. 1. — P. 46–49.

Study of the light-induced aggregation of photochromic spiral compounds / R. E. Karpov, V. A. Barachevskii, Y. P. Strokach et al. // Zhurnal Nauchnoi I Prikladnoi Fotografii. — 2003. — Vol. 48, no. 5. — P. 33–43.

Supramolecular architecture of crown-containing styryl dyes: Part i. crystal and molecular structures of the acetonitrile solvate monohydrate of the potassium iodide complex with benzo-15-crown-5 ether dye based on methylquinoline iodide / L. G. Kuz'mina, A. V. Churakov, J. A. Howard et al. // Crystallography Reports. — 2003. — Vol. 48, no. 4. — P. 613–622. The structure of a single crystal of the acetonitrile solvate monohydrate of the potassium iodide complex with benzo-15-crown-5 ether dye based on methylquinoline iodide (I) is determined by X-ray diffraction. It is established that the single crystal contains positively charged molecules of benzocrown ether photodye (D), K+ cations, I- anions, and water and acetonitrile solvate molecules in the ratio 1 : 0.5 : 1.5 : 1 : 1, respectively. The K+ cation and one of the I(-)anions occupy special positions along the twofold axis. The K+ cation is coordinated by ten oxygen atoms of the crown ether fragments of two D molecules to form the [D2K](3+) complex. Inside the complex, two aromatic quinoline fragments are involved in a stacking interaction. The crossed mutual arrangement of the ethylene fragments and the considerable distance between them exclude the occurrence of intramolecular photochemical [2 + 2]cycloaddition reactions. In the crystal, the [D2K](3+) cationic complexes form stacks along the b axis. The adjacent complexes in a stack are related through the center of symmetry and, therefore, are arranged in a head-to-tail manner. The double bonds of the neighboring molecular cations D in a stack are strictly parallel to each other and are separated by a distance of 3.754 Angstrom. This geometry is favorable to the intermolecular cycloaddition reaction that should result in the formation of the syn head-to-tail isomer. (C) 2003 MAIK "Nauka/Interperiodica". [ DOI ]

Synthesis, photochromic behaviour and light-controlled complexation of 3,3-diphenyl-3h-benzo[f]chromenes containing a dimethylamino group or an aza-15-crown-5 ether unit / O. A. Fedorova, F. Maurel, E. N. Ushakov et al. // New Journal of Chemistry. — 2003. — Vol. 27, no. 12. — P. 1720–1730. Synthesis of 3,3-diphenyl-3H-benzo[f]chromenes containing an aza-15-crown-5-ether unit or a dimethylamino group and spectrokinetic study of light-controlled complexation of these compounds with Ca2+ in acetonitrile are reported. The affinity of the azacrown chromene to Ca2+ decreases substantially upon a photoinduced ring-opening reaction. In contrast, dimethylamino chromene, which is unable to bind Ca2+ in the dark, shows a low cation-binding capacity upon UV irradiation. The spectroscopic and kinetic behaviour of the photomerocyanine isomers of these chromenes is strongly affected by complexation with Ca2+. A semi-empirical quantum-chemical study of the merocyanine isomers was applied to interpret the experimental data. [ DOI ]

A facile method for the synthesis of benzothiacrown ether formyl derivatives / O. A. Fedorova, A. I. Vedernikov, O. V. Yescheulova et al. // Synthetic Communications. — 2002. — Vol. 32, no. 12. — P. 1909–1915. A facile route to the formyl derivatives of benzothiacrown ethers with different combinations of O and S heteroatoms in the macrocycle involving ring closure reactions of substituted benzaldehydes with dithiols was developed. The effects of alkali metal cations and solvent were studied. [ DOI ]

Anion-capped benzodithia-18-crown-6 styryl dye monolayers / S. Y. Zaitsev, T. I. Sergeeva, E. A. Baryshnikova et al. // Colloids and Surfaces A: Physicochemical and Engineering Aspects. — 2002. — Vol. 198. — P. 473–482. The anion-capped amphiphilic benzodithia-18-crown-6 styryl dye forms relatively stable insoluble monolayers on distilled water (collapse pressure is 25.5 mN m(-1)) and aqueous solutions containing alkali (25.3-26.4 mN m(-1)) and heavy metals (49.0 mN m(-1) for Ag+). Two types of the dye monolayer structures (depending on alkali metal or heavy metal cations present in the aqueous subphase) have been discriminated from surface pressure-molecular area and surface potential-molecular area isotherms, The ionoselective and photosensitive properties of the amphiphilic dye in monolayers have been studied in the presence of K+, Na+, Mg+, Ca+ or Ag+ cations in the aqueous subphase. (C) 2002 Elsevier Science B.V. All rights reserved. [ DOI ]

Antimutagenic activity of crown-containing compounds / G. D. Zasukhina, I. M. Vasil'eva, A. D. Durnev et al. // Doklady Biological Sciences. — 2002. — Vol. 384. — P. 257–259. Two crown-contg. compds. B (N-carboxymethylaza-15-crown-5 compd.) and compd. C (N-carboxymethylbenzoaza-15-crown-5 compd.) were synthesized and evaluated for their effect on DNA lesions induced by different mutagens in a transplantable human cell culture. Results indicate that compds. B and C possess antimutagenic activity whose expression is not related to their antioxidant effects protecting DNA against the prooxidant activity of mutagens.

Crown-containing spironaphthoxazines and spiropyrans 3. synthesis and investigation of the merocyanine form of crown-containing spirobenzothiazolinonaphthoxazine / O. A. Fedorova, A. V. Koshkin, S. P. Gromov et al. // Russian Chemical Bulletin. — 2002. — Vol. 51, no. 8. — P. 1441–1450. A method for the synthesis of the spirobenzothiazolinonaphthoxazine, stable in the merocyanine form and containing a crown-ether fragment was developed. The complexing properties of the prepared merocyanine compound and the spectroscopic and photochromic characteristics of its complexes with alkaline earth metal cations were studied by NMR and UV spectroscopy. The results were analyzed using quantum-chemical calculations. The addition of alkaline earth metal perchlorates to a solution of a crown ether-containing merocyanine dye in MeCN results in the coordination of metal cations to two binding centers, namely, the crown-ether fragment and the merocyanine oxygen atom. This gives rise to two types of complexes, which differ substantially in their structurally. The complexation. induces changes in the UV spectra and influences on the photochromic behavior of the prepared compound. [ DOI ]

Crown-containing spironaphthoxazines and spiropyrans. 2. influence of metal cations on the photochromic properties of spironaphthoxazines linked with aza-15(18)-crown-5(6) ethers / Y. P. Strokach, O. A. Fedorova, S. P. Gromov et al. // Russian Chemical Bulletin. — 2002. — Vol. 51, no. 1. — P. 58–66. Spironaphthoxazines linked with aza-15(18)-crown-5(6) fragments were synthesized and studied for the first time. Addition of alkaline-earth cations to solutions of crown-containing spironaphthoxazines causes a hypsochromic shift of the absorption hand of I lie spiro form and a bathochromic shift oft tie absorption band of the merocyanine form, shifts the equilibrium to the merocyanine form, and changes the lifetime of the photoexcited merocyanine form. The spectral and kinetic data were Used to propose a mechanism of complexation and calculate the stability constants of the resulting complexes. The complexation involves the crown fragment and the merocyanine oxygen atom. The type of the complex is determined by the cation nature and size. [ DOI ]

Effect of a polymer matrix on the complexation and photochemical behavior of an azacrown-containing styryl dye / I. R. Nasimova, E. N. Ushakov, E. E. Makhaeva et al. // Polymer Science, Series A. — 2002. — Vol. 44, no. 12. — P. 1313–1318. The effect of the polymer matrix of neutral poly(N-vinylcaprolactam) gels on the complexation and photochemical behavior of a styryl dye containing the N-phenylaza-18-crown-6 moiety was studied. The electronic absorption spectra of the dye immobilized in the polymer matrix and its solution in acetonitrile were found to differ only slightly. Polymer matrix subchains are conformationally insensitive to immobilization of the dye. The addition of barium perchlorate to the polymer-dye-acetonitrile system results in strong swelling of the polymer gel. The polymer network impedes the complexation between the crown ether moiety of the dye and the barium cation because of possible interactions of Ba2+ with one or more C=O groups of poly(N-vinylcaprolactam). A high degree of transformation of the immobilized dye to the metal complex form is attainable at relatively high concentrations of the metal salt when the molar ratio of Ba(ClO4)(2) to vinylcaprolactam units approaches unity. It was shown that the dye undergoes reversible trans-cis photoisomerization and dark (thermal) cis-trans isomerization in both the swollen gel and dry polymer films.

Effect of metal cations on the photochromic properties of spironaphthoxazines conjugated with aza-15(18)-crown-5(6) ethers / O. A. Fedorova, Y. P. Strokach, S. P. Gromov et al. // New Journal of Chemistry. — 2002. — Vol. 26, no. 9. — P. 1137–1145. Spironaphthoxazines conjugated with aza-15(18)-crown-5(6)-ether moieties at the 6'-position of the naphthalene fragment (crown-containing spironaphthoxazine, CSN) were synthesised and studied for the first time. The addition of Li+ and alkaline earth (Mg2+, Ca2+, Sr2+ and Ba2+) metal cations to CSN solutions results in a hypsochromic shift of the UV absorption band of the spiro form and a bathochromic shift of the absorption band of the merocyanine form in the visible region. In addition, the equilibrium shifts to the merocyanine form, and the lifetime of the photoinduced merocyanine form increases. Analysis of the spectral and kinetic data allows a complexation scheme to be proposed and the stability constants of the resulting complexes to be calculated. According to the results obtained, the complexation with Li+ and alkaline earth metal cations in acetonitrile initially involves the crown ether moiety; the participation of the merocyanine oxygen atom in the complexation process occurs at a high metal cation concentration. The UV-induced isomerisation of CSN into the merocyanine form causes a decrease of the cation binding ability. [ DOI ]

Simulation of optical response to complex formation of crown-containing 2-styrylbenzothiazoles with alkaline-earth metals / Y. V. Fedorov, O. A. Fedorova, S. P. Gromov et al. // Russian Chemical Bulletin. — 2002. — Vol. 51, no. 5. — P. 789–795. The photochromic properties and complex formation of 2-styrylbenzothiazoles containing different crown ether moieties with alkaline-earth metals were described using optical methods, NMR spectroscopy, and HPLC. The large ionochromic effect and fluorescence quenching on complex formation with alkali-earth metal cations were found for 2-styrylbenzothiazole containing the phenylazacrown ether moiety. The small ionochromic effect and fluorescence enhancement of complex formation with alkali-earth metal cations were found for 2-styrylbenzothiazole containing the benzocrown ether moiety. cis-isomers of 2-styrylbenzothiazoles were stable in the dark in acetonitrile. The method for separation of cis-isomers of 2-styrylbenzothiazoles by HPLC was proposed. [ DOI ]

Supramolecular assemblies of photochromic benzodithia-18-crown-6 ethers in crystals, solutions, and monolayers / O. A. Fedorova, Y. V. Fedorov, A. I. Vedernikov et al. // New Journal of Chemistry. — 2002. — Vol. 26, no. 5. — P. 543–553. We studied the assembly of dithiacrown ether styryl dye (CSD) molecules in crystals, solutions, and films in the presence of metal cations. X-Ray diffraction data allowed us to conclude that the anion affects the supramolecular architecture of CSDs in the crystal, specifically, the type of stacking of the dye molecules. In solution, in the presence of Pb2+, CSD molecules with the betaine structure spontaneously form dimeric complexes consisting of two dye molecules and two metal cations, with a fixed mutual arrangement of the double bonds. The dimer complex is stable due to coordination between the anion substituent of one molecule and the metal cation located in the crown ether cavity of the other molecule. Irradiation of the dimer complexes leads to regio- and stereoselective [2+2]-cycloaddition, giving only one cyclobutane derivative of the eleven theoretically possible products. The other photoreaction studied for CSDs is reversible Z-E isomerization. Due to its specific structure, the betaine-type CSD is able to form the anion-capped Z-isomer. Intramolecular coordination in the 'anion-capped' isomer enhances its stability and causes a sharp deceleration of its dark Z-E isomerization. The amphiphilic CSD forms relatively stable monolayers on distilled water and various aqueous salt subphases. The results obtained indicate that it is possible to distinguish between two types of the dye monolayer structures based on the presence of alkali or heavy metal cations in the aqueous subphase. [ DOI ]

Synthesis of crown-containing 2-styrylbenzothiazoles. effect of alkali metal cations on the condensation of crown-ether benzaldehydes with 2-methylbenzothiazole / O. A. Fedorova, E. N. Andryukhina, A. V. Lindeman et al. // Russian Chemical Bulletin. — 2002. — Vol. 51, no. 2. — P. 319–325. Methods for the synthesis of unknown 2-styrylbenzothiazoles containing crown ether moieties with different combinations of O, S, and N-heteroatoms based on the Wittig reaction or condensation of 2-methylbenzothiazole with crown-ether benzaldehydes in the presence of strong bases or acids are proposed. The condensation in the presence of bases is accompanied by complex formation with participation of the crown ether moiety of the benzaldehyde. The complex formation has a pronounced influence on the yield of the target product and the pattern of condensation of 2-methylbenzothiazole with crown-ether benzaldehydes. [ DOI ]

Thiacrown ether substituted styryl dyes: Synthesis, complex formation and multiphotochromic properties / O. A. Fedorova, Y. V. Fedorov, A. I. Vedernikov et al. // The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. — 2002. — Vol. 106, no. 25. — P. 6213–6222. Syntheses of two series of new styryl dyes incorporating thiacrown ether moieties (CSDs 3a-e, 4a-e) are described. H-1 NMR and UV-vis measurements show that these compounds exhibit a strong preference for formation of complexes with heavy metal ions. Polarographic measurements allow conversion of relative complex formation stability constants, determined spectrophoto metrically. into absolute values. The photochromic properties of the CSDs are based on reversible trans-cis isomerization and [2+2]-photocycloaddition. The influences of the terminal group of the N-substituent and of the size and composition of the crown ether cavity on metal cation complexation selectivity and on photochromism are evaluated. [ DOI ]

Fedorova O. A., Gromov S. P., Alfimov M. V. Cation-dependent pericyclic reactions of crown-containing photochromic compounds // Russian Chemical Bulletin. — 2001. — Vol. 50, no. 11. — P. 1970–1983. The review is devoted to the photochromism of pericyclic reactions of crown-containing photochromic systems, The complex formation of photochromic crown ethers with metal cations has a substantial effect on both the spectral characteristics of molecules and occurrence of photochromic reactions. A possibility to create systems with photocontrolled complex-forming properties is an attractive feature of the novel systems. [ DOI ]

Sers spectroscopy study of merocyanine form of spironaphthoxazine derivatives / A. V. Feofanov, Y. S. Alaverdian, S. P. Gromov et al. // Journal of Molecular Structure. — 2001. — Vol. 563. — P. 193–197. Merocyanine (MC) form of spironaphthoxazine (1) as well as its morpholine (2) and aza- 15-crown-5-ether (3) 6'-derivatives was studied by using the surface-enhanced Raman scattering (SERS) spectroscopy. Characteristic bands were revealed that were sensitive to interactions of MC oxygen and to the configuration of the molecule with respect to the =C-N= bridge between naphthalene and indolinic chromophores. The single isomer was detected for 1 and 1Eu(3+) complex in acetonitrile and for 1 in ethanol. It was ascribed to TTC (trans-trans-cis) form. Two isomers of 2 and 3 (TTC and CTC) coexisted in acetonitrile, ethanol and methanol, whereas CTC form was only present for 2 and 3 in 2,2.2-trifluoroethanol and fur complexes of 2 and 3 with metal cations: (Ba2+, Mg2+, Eu3+) in acetonitrile. The MC oxygen of 2 and 3 was found to be protonated in 2,2,2-trifluoroethanol. (C) 2001 Elsevier Science B.V. All rights reserved. [ DOI ]

Fedorova O. A., Gromov S. P. Cation-dependent pericyclic reactions of photochromic crown ethers // Targets in Heterocyclic Systems. — Vol. 4. — Societa Chimica Italiana, 2000. — P. 205–229. The review describes the photochromism of crown-ether systems based on pericyclic reactions. The photochromic transformations and the obsd. spectral changes or changes in phys. or chem. behavior are related to the modification of the system geometry and electron distribution. A novel approach to the modification of photochromic systems includes the exploration of the complex formation process in crown ether contg. photochromic systems. The results obtained show that the introduction of crown-ether moieties into dye mols. affords compds. that can change their spectral and photochromic properties upon complex formation. The approach offers the possibility of synthesizing new photochromic substances characterized by enhanced photostability, high sensitivity, and a broad range of operating wavelengths. Yet another important feature of the novel systems is reversible change in the capacity of a photochromic host mol. for assocn. with guests upon irradn. The researches believe that the novel photochromic systems can now be regarded as being promising for traditional applications (photochromic ophthalmic lenses or camera filters, reversible holog. systems, cosmetics) and for mol. electronics, biomimetic chem., and optical information storage. A review with 55 refs.

Langmuir films of the novel anion-capped amphiphilic benzodithia-15-crown-5 dye / S. Y. Zaitsev, E. A. Baryshnikova, T. I. Sergeeva et al. // Thin Solid Films. — 2000. — Vol. 372, no. 1-2. — P. 230–236. The novel anion-capped amphiphilic benzodithia-15-crown-5 styryl dye forms relatively stable insoluble monolayers on distilled water (collapse pressure is approx. 35 mN/m) and on the aqueous subphases containing alkali metal cations (38 mN/m) or heavy metal cations (33 or 31 mN/m for Ag+ or Hg2+), respectively. Two types of the dye-cation complexes, depending on the nature of a particular cation in the aqueous subphase, have been distinguished by measuring surface pressure-molecular area and surface potential-molecular area isotherms, as well as observed by Brewster angle microscopy. The surface-active and spectroscopic properties of the amphiphilic dye in monolayers in the presence of K+, Na+, Ca2+, Mg2+, Ag+ or Hg2+ cations in the aqueous subphases have been studied. (C) 2000 Elsevier Science S.A. All rights reserved. [ DOI ]

Monolayers of the photosensitive benzodithia-15-crown-5 derivative / S. Y. Zaitsev, E. A. Baryshnikova, T. A. Sergeeva et al. // Colloids and Surfaces A: Physicochemical and Engineering Aspects. — 2000. — Vol. 171, no. 1-3. — P. 283–290. The amphiphilic benzodithia-15-crown-5 styryl dye forms relatively stable insoluble monolayers on distilled water (collapse pressure is 34.5 mN m(-1)) and alkali metal cations (35.6-36.7 mN m(-1)) or heavy metal cations (24.2 mN m(-1) for Ag+) in the aqueous subphase. Three types of the dye monolayer structures depending on the subphase nature (water, alkali metal or heavy metal cations) have been distinguished from surface pressure-molecular area and surface potential-molecular area isotherms, as well as observed by Brewster angle microscopy (BAM). The ionoselective and photosensitive properties of the amphiphilic dye in monolayers have been studied in the presence of K+, Na+, Hg2+ and Ag+ cations in the aqueous subphases. (C) 2000 Elsevier Science B.V. All rights reserved. [ DOI ]

Novel azacrown ether-containing spiro[indoline-2,3 '-naphthoxazines]: design, synthesis and cation-dependent photochromism / O. A. Fedorova, S. P. Gromov, Y. V. Pershina et al. // Journal of the Chemical Society. Perkin Transactions 2. — 2000. — no. 3. — P. 563–570. Novel spironaphthoxazine compounds with an aza-15-crown-5 ether fragment at position 5' or 9' of the naphthalene ring were synthesised. Spectrokinetic measurements showed the occurrence of two competing formation processes for complexation with alkaline earth or rare earth metal cations. A comparative study of the prepared compounds demonstrated the role of molecular design and the metal cation nature in the cation-dependent photoinduced transformation of spiro[indoline-naphthoxazines]. [ DOI ]

Synthesis of amphiphilic photochromic benzo-15(18)-crown-5(6) ethers and their study in monolayers / O. A. Fedorova, S. P. Gromov, O. V. Eshcheulova et al. // Bioorganicheskaya Khimiya. — 2000. — Vol. 26, no. 9. — P. 707–717. New amphiphilic photochromic benzo-15(18)-crown-5(6) ethers (APC) differing in the position of the octadecyl substituent and the size of the crown cavity were synthesized. The compounds form stable monolayers in the air/water and air/alkaline metal salt solution interfaces. The results of the pressure isotherm measurements, atomic force microscopy (AFM), and electronic spectroscopy show that the structure of the monolayers formed depends on the structure of the parent APC and the nature of the cation in salt solutions. The area per molecule of APC in the monolayer (specific area) is the smallest on the water surface and increases by 20-40% on the aqueous subphase surface with an increasing concentration of salts therein to indicate the formation of APC complexes with the metal cations. When the hydrophobic aliphatic substituent is displaced from position 3 to position 5 of the benzothiazole ring, the specific area on the surface of water and subphases decreases twofold, which indicates the compactization of the monolayer on this modification, A reversible E-Z-photoisomerization of APC was found in the monolayers formed in the salt solution/air interface. The features of the reaction are defined by the specific organization of the amphiphilic molecules in the monolayer and by the nature of the cation.

Template effect in the synthesis of formyl derivatives of benzothiacrown compounds / O. A. Fedorova, A. I. Vedernikov, O. V. Yescheulova et al. // Russian Chemical Bulletin. — 2000. — Vol. 49, no. 11. — P. 1853–1858. The condensation of 3,4-bis(2-haloethoxy)benzaldehydes with acyclic alpha,omega -alkanedithiols in the presence of alkali metal carbonates in dry ethanol, DMF, MeCN and their mixtures with water gives formyl derivatives of benzothiacrown compounds in high yields. The best results are attained when the radius of the hydrated metal cation fits to the crown ether cavity. In the ease of Cs+, high yields were observed for crown ethers of any size and composition: this can be explained by a specific template effect of this cation. The influence of the nature of the leaving group in 3,4-bis(2-haloethoxy)benzaldehydes was established for reactions with dithiols containing no ether oxygen atoms. [ DOI ]

Carboxylic groups as cofactors in the lanthanide-catalyzed hydrolysis of phosphate esters. stabilities of europium(iii) complexes with aza-benzo-15-crown-5 ether derivatives and their catalytic activity vs bis(p-nitrophenyl)phosphate and dna / A. Roigk, O. V. Yescheulova, Y. V. Fedorov et al. // Organic Letters. — 1999. — Vol. 1, no. 6. — P. 833–835. [GRAPHICS] The stability of europium(III) complexes with benzocrown ether derivatives 2-4 containing carboxylic functions with methylene spacers of different length was found to vary surprisingly little. In sharp contrast, the hydrolytic activity of these catalysts against bis(p-nitrophenyl)-phosphate (BNPP) varied by a factor of 30. The results show for the first time the efficiency of the carboxylic group as cofactor in phosphate ester hydrolysis, which until now was established only in some enzymes, Other than with BNPP, the hydrolysis with plasmid DNA (nicking experiments) showed no rate enhancement. [ DOI ]

Crown-containing spirooxazines and spiropyrans - 1. synthesis and the anion-"capped" complexes of photochromic aza-15-crown-5 ethers with flexible spacers / O. A. Fedorova, S. P. Gromov, Y. P. Strokach et al. // Russian Chemical Bulletin. — 1999. — Vol. 48, no. 10. — P. 1950–1959. Methods for the synthesis of new spironaphthooxazines containing an aza-15-crown-5 fragment in two different positions (5' and 9') were developed. The spectral and photochemical properties of these compounds suggest that two competitive complexation processes occur with alkaline-earth or rare-earth metal cations differing in efficiency and selectivity. A metal cation occupies the optimum position in the crown-ether cavity with respect to the donor oxygen atom of the merocyanine form of the dye and thus can affect more strongly its spectral and photochemical properties than in the case of intermolecular interaction. [ DOI ]

Crown-containing styryl dyes: cation-induced self-assembly of multiphotochromic 15-crown-5 ethers into photoswitchable molecular devices / E. N. Ushakov, S. P. Gromov, A. V. Buevich et al. // Journal of the Chemical Society. Perkin Transactions 2. — 1999. — no. 3. — P. 601–607. [ DOI ]

Femtosecond spectrochronography of the reverse photochromic transition in derivatives of spiro compounds / M. V. Alfimov, A. V. Balakin, S. P. Gromov et al. // Russian Journal of Physical Chemistry A. — 1999. — Vol. 73, no. 10. — P. 1685–1694. The photochromic properties of the merocyanines of a spiropyran, a spironaphthooxazine and a crown-containing spironaphthooxazine as well as complexes of these compounds with metal ions were studied. Various mechanisms for the reverse photochromic transition and the possibility of dissociation of the ionic complexes under the action of femtosecond-scale light pulses were discussed. A kinetic model describing the experimental results was developed under the assumption that the process of isomerization plays the main role in the cycle of photochemical transformations.

Photoswitchable molecular pincers: synthesis, self-assembly into sandwich complexes and ion-selective intramolecular [2+2]-photocycloaddition of an unsaturated bis-15-crown-5 ether / S. P. Gromov, O. A. Fedorova, E. N. Ushakov et al. // Journal of the Chemical Society. Perkin Transactions 2. — 1999. — no. 7. — P. 1323–1329. [ DOI ]

Sandwich-type complexes of alkaline-earth metal cations with a bisstyryl dye containing two crown ether units / E. N. Ushakov, S. P. Gromov, O. A. Fedorova et al. // The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. — 1999. — Vol. 103, no. 50. — P. 11188–11193. The formation of complexes between a bisstyryl dye containing two benzo-15-crown-5 ether groups, 2, and Mg2+, Ca2+, Sr2+, and Ba2+ ions was studied in acetonitrile solution by using a spectrophotometric approach. In contrast to its monostyryl analogue 1, which shows a rather low cation-binding selectivity, the bisstyryl dye 2 selectively binds the Sr2+ and Ba2+ ions because of formation of intramolecular sandwich complexes. Alkaline-earth metal cations induce substantial blue shifts of the absorption maximum of 1 and 2, particularly in the case of sandwich complex formation. The emission behavior of 1 and 2 and their Ba2+ complexes in acetonitrile solution has also been studied. In both cases, complex formation leads to a blue shift of the fluorescence maximum and a decrease in the emission quantum yield. The fluorescence decay is monoexponential for the complex of 1 and biexponential for that of 2. The longer-lived fluorescence component, which corresponds to the lower-energy band in the steady-state spectrum, is assigned to an intramolecular excimer state. [ DOI ]

Synthesis and monolayer study of a new amphiphilic photochromic crown-ether / S. Y. Zaitsev, T. I. Sergeeva, E. A. Baryshnikova et al. // Materials Science & Engineering C-Biomimetic and Supramolecular Systems. — 1999. — Vol. 8. — P. 469–473. The ionoselective and photosensitive properties of the new amphiphilic crown-ether dye {perchlorate of 2-[(E)-2-(2,3,5,6,8,9,11,12-octahydro- 1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl)]-5-octadecanoylamino-3-ethyl-1,3-benzothiazolium} in monolayers have been studied. The collapse pressure of the dye monolayers is about 53 mN/m on distilled water, slightly increases up to 57-59 mN/m in the presence of Na+, Ca2+, Mg2+ cations and significantly decreases up to 43-44 mN/m in the presence of K+ cations in the aqueous subphases. The area per dye molecule in monolayer is the smallest on water and increases with increasing of the salt concentration in the aqueous subphase. These are evidences for the existence of the dye-cation complexes in monolayers. The reversible changes of the reflection intensity (irans-cis-trans isomerization) by dye photoactivation can be observed only for the dye-cation complexes at very low surface pressure in the liquid-expanded state of monolayers. The changes of the reflection intensity by photoactivation in the Liquid-condensed state of the dye monolayers on KCl solution are found irreversible that may be due to the photodimerization of the dye to cyclobutane. (C) 1999 Elsevier Science S.A. All rights reserved. [ DOI ]

Synthesis, structure, and ion selective complexation of trans and cis isomers of photochromic dithia-18-crown-6 ethers / M. V. Alfimov, S. P. Gromov, Y. V. Fedorov et al. // Journal of the American Chemical Society. — 1999. — Vol. 121, no. 21. — P. 4992–5000. Photochromic styryl dyes containing benzodithia-18-crown-6 and N-substituted benzothiazolium moieties are synthesized and characterized spectroscopically and, for a specific case, by X-ray crystallography. The effects of the N-substituent and of sulfur atom substitution in the crown ether cavity on metal cation complex formation and on photochromism due to reversible trans-cis photoisomerization are evaluated. High selectivities for heavy metal ions, such as Ag+ and Hg2+, are observed, in contrast to the benzo-18-crown-6 dyes which selectively bind alkali and alkali earth cations. Relative complex formation stability constants, determined spectrophotometrically, are converted to absolute values by polarographic measurements. The stability constant for Hg2+ complex formation by the trans dye is enhanced 47-fold upon substitution of the 4-butylsulfonate group for methyl at the nitrogen of the benzothiazolium moiety. Photoisomerization to the cis dye is accompanied by a further 11-fold stability constant increase and by spectral changes that are consistent with formation of an ion-"capped" complex, involving intramolecular coordination of the sulfonate anion to Hg2+. Addition of a large excess of Mg2+ ions disrupts this intramolecular coordination bond without displacing the Hg2+ ion from the dithiacrown ether cavity. [ DOI ]

Crown ether styryl dyes - 24. synthesis of multiphotochromic 15-crown-5 ethers with rigid spacers, their anion-"capped" complexes, and stereospecific [2+2] autophotocycloaddition / S. P. Gromov, O. A. Fedorova, E. N. Ushakov et al. // Russian Chemical Bulletin. — 1998. — Vol. 47, no. 1. — P. 97–106. [ DOI ]

Monolayers of an amphiphilic crown-ether styryl dye / S. Y. Zaitsev, S. P. Gromov, O. A. Fedorova et al. // Colloids and Surfaces A: Physicochemical and Engineering Aspects. — 1998. — Vol. 131, no. 1-3. — P. 325–332. The crown-ether styryl dye (I) was synthesized and its monolayers were prepared. The surface-active and optical properties of dye I were investigated. The surface pressure-molecular area and surface potential-molecular area isotherms for mixed monolayers of dye I and dipalmitoylphosphatidic acid at various aqueous salt subphases were measured. (C) 1998 Elsevier Science B.V. [ DOI ]

Photosensitive and ionoselective properties of the amphipilic crown-ether dye in monolayers / S. Y. Zaitsev, V. P. Vereschetin, E. A. Baryshnikova et al. // Thin Solid Films. — 1998. — Vol. 327. — P. 821–823. Monolayers of the amphiphilic benzo-15-crown-5 styryl dye were prepared. Their ionoselective and photosensitive properties in the presence of K+ or Na+ cations in the aqueous subphases were investigated. The reversible changes of the reflection intensity (due to trans-cis-trans isomerization of the C=C bound in dye molecule) can be observed only for complexes of the dye molecules in monolayers with cations from the aqueous subphase. (C) 1998 Elsevier Science S.A. All rights reserved. [ DOI ]

A surface-enhanced raman spectroscopic study of novel photochromic benzodithiacrown ether styryl dyes / M. V. Alfimov, Y. V. Fedorov, O. A. Fedorova et al. // Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy. — 1997. — Vol. 53, no. 11. — P. 1853–1865. Surface-enhanced Raman scattering (SERS) and surface-enhanced resonance Raman scattering (SERRS) spectra of two benzothiazolium styryl dyes containing a crown ether ring with sulfur and oxy obtained at low concentration (10(-5)-10(-7) M) in the presence of silver colloids. A preliminary assignment of the observed bands to particular vibrational modes has been made by comparison of infrared (IR), normal Raman (R) and SERS data obtained from thiacrown ether and benzothiazolium molecular fragments with SERRS spectra of a benzothiazolium styryl dye containing a normal crown ether ring and with assignments reported previously for related molecules. The results indicate that the sulfur atoms of both the benzothiazolium and the dithiacrown ether groups participate in adsorption at the silver surface; possible models of adsorption of these dyes and their fragments are discussed. (C) 1997 Elsevier Science B.V. [ DOI ]

Complexation of photochromic crown ether styryl dyes with mg2+ as probed by surface-enhanced raman scattering spectroscopy / A. Feofanov, A. Ianoul, S. Gromov et al. // Journal of Physical Chemistry B. — 1997. — Vol. 101, no. 20. — P. 4077–4084. Complexation with magnesium cations of 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin (1), as well as derivatives of crown ether styryl dyes perchlorate 2-[2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-16-yl)ethenyl]-3-ethylbenzothiazolium (2), betaine 2-[2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-16-yl)ethenyl]-3-(3-sulfopropyl)-benzothiazolium (3), betaine 2-[2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-16-yl)ethenyl]-3-(3-sulfoethyl)benzothiazolium (4) was studied by surface-enhanced Raman scattering (SERS) spectroscopy. Comparative studies of isomerization and complexation of photochromic ionophores 2-4 with Mg2+ in solution and when adsorbed on the silver surface were performed. The aim was to characterize parameters of these processes depending on the nature (alkyl versus sulfo-alkyl) as well as the length (sulfoethyl versus sulfopropyl) of the N substituent in the benzothiazolium residue. The data obtained indicate stabilization of the trans conformation and prevention of the trans-cis isomerization for the adsorbed molecules as well as for their complexes with Mg2+ due to fast nonradiative energy transfer from the dye excited state to metal surface. Adsorption of a dye having initially cis conformation in solution is accompanied by surface-induced cis-trans relaxation. Adsorption constants calculated from the Langmuir isotherms revealed slightly preferential adsorption of 2-4 complexed with Mg2+ as compared to the free dyes. Desorption of the dyes was found to occur on the hours time scale, whereas reversible capture/release of metal ions by adsorbed molecules is quite fast and may serve as an indicator of a cation level and/or complexation processes in bulk solution. The SERS titration procedure was developed permitting the complexation of the ionophores with metal cations to be followed and equilibrium constants of these processes to be measured in a wide range (down to 10(-7) M) of ligand concentrations. By the measurement of the equilibrium constants, adsorption on the silver surface was concluded not to affect the complexation of 1 and trans-2 with Mg2+. Association of the Mg2+ cation with the sulfonate group was found to be more favorable than binding with the crown ether moiety for the adsorbed (trans-3)Mg2+ and (trans-4)Mg2+ complexes. Appearance of the (trans-3)(Mg2+)(2) and (trans-4)(Mg2+)(2) species was detected in the solution at increased metal/ligand molar ratios. These complexes were found to be unperturbed if absorbed on the silver surface. Since the measurement of equilibrium constants are intractable by other techniques, measuring equilibrium constants for (trans-3)(Mg2+)(2) and (trans-4)(Mg2+)(2) complexe formation is readily acquired by SERS spectroscopy. [ DOI ]

Crown ether styryl dyes - 23. synthesis and complexation of cis-isomers of photochromic dithia-15(18)-crown-5(6) ethers / M. V. Alfimov, A. I. Vedernikov, S. P. Gromov et al. // Russian Chemical Bulletin. — 1997. — Vol. 46, no. 12. — P. 2099–2106. A novel styryl dye containing benzodithia-18-crown-6 and N-(4-sulfobutyl)benzothiazolium fragments was synthesized. The complex formation of the cis-isomers of several photochromic styryl dyes containing dithia-15(18)-crown-5(6) fragments with Hg2+ and Mg2+ ions was studied. The stability constants of the complexes with Mg2+ and the relative stability constants of the complexes with Hg2+ (with respect to benzo-1,10-dithia-18-crown-6 ether) were measured. The fact that the stability constant increases 11-fold on going from the trans- to the corresponding cis-isomer was attributed to the formation of an anion-"capped" complex. [ DOI ]

Crown ether styryl dyes .21. synthesis, spectral properties, and complex formation of trans-isomers of the chromogenic dithia-15(18)-crown-5(6) ethers / S. P. Gromov, O. A. Fedorova, A. I. Vedernikov et al. // Russian Chemical Bulletin. — 1997. — Vol. 46, no. 5. — P. 967–974. Novel styryl dyes containing dithia-15(18)-crown-6(5)-ether moieties were synthesized. Their selective complex formation with Hg2+ and Ag+ ions was studied by (0)1H NMR and electronic spectroscopy; the stability constants of the Ag+ complexes and the relative stability constants (in relation to benzodithia-18-crown-6) of the Hg2+ complexes were determined. The chemical shifts of the beta,beta'-protons in the CH2S group change upon the complex formation in parallel with the logK(1) values of the complexes. [ DOI ]

Crown ether styryl dyes .22. synthesis and complexation of the cis-isomers of photochromic aza-15-crown-5 ethers / S. P. Gromov, E. N. Ushakov, O. A. Fedorova et al. // Russian Chemical Bulletin. — 1997. — Vol. 46, no. 6. — P. 1143–1148. New crown ether-containing styryl dyes of the benzothiazole series containing an aza-15-crown-5-ether moiety were synthesized. The trans-cis-photoisomerization of these dyes and their analogs was studied; the effect of metal cations on the kinetics of dark cis-trans-isomerization was elucidated. The stability constants of the complexes of the cis-isomers of these dyes with Ca(ClO4)(2) were estimated. The dramatic increase (by more than three orders of magnitude) in the stability of the complexes on passing from a cationic dye to a betaine was attributed to the formation of an intramolecular bond in the cis-complexes between the sulfo group of the N-substituent and the metal cation located in the cavity of the azacrown-ether moiety. [ DOI ]

Crown-containing styryl dyes .19. complexation and cation-induced aggregation of chromogenic aza-15-crown-5-ethers / E. N. Ushakov, S. P. Gromov, O. A. Fedorova, M. V. Alfimov // Russian Chemical Bulletin. — 1997. — Vol. 46, no. 3. — P. 463–471. Complexation of styryl dyes containing the N-phenylaza-15-crown-5 fragment (trans-2a,b) with Ca2+ ions in MeCN was studied. Unlike cationic dye trans-2a, betaine trans-2b forms both complexes of 1:1 stoichiometry and aggregates consisting of four dye molecules and one Ca2+ ion. Cation-induced aggregation was observed also for the analog of dye trans-2b, which contains a dimethylamino group instead of an azacrown ether fragment (trans-3). Apparently, the interaction between a metal cation and sulfo groups of molecules trans-2b or trans-3 makes the main contribution to the stability of aggregates. The dependence of the stability of aggregates on the nature of the metal cation was studied. [ DOI ]

Photochromic crown ethers .1. formation of ion pairs, trans-cis-isomerization, and metal ion binding in a nonpolar medium / V. P. Tsybyshev, V. A. Livshits, B. B. Meshkov et al. // Russian Chemical Bulletin. — 1997. — Vol. 46, no. 7. — P. 1239–1244. An amphiphilic crown-containing styryl dye (1) was synthesized, and the effects of irradiation, temperature, and alkali and alkali-earth metal ions on the conductivity and optical spectra of its solutions in dioctyl phthalate were studied. Compound 1 in the transform almost completely exists as ion pairs (IF). Irradiation at a long-wavelength absorption maximum (lambda(max)) results in a reversible increase in the conductivity and, hence, a degree of dissociation of IP (alpha); these parameters decrease when complexes with metal ions are formed. The relaxation times for the photoinduced conductivity coincide with a decrease in the extinction within experimental error in the 20-60 degrees C temperature range. The photoinduced increase in alpha is caused by trans-cis-isomerization and an increase in steric hindrances for the interaction of the ClO4- anion with the N+ atom of benzothiazolium in the cis-form of 1. The activation energies for the dark cis-trans-relaxation, absolute alpha values, and thermodynamic parameters of dissociation of IP in the trans-form, as well as the alpha values in a photostationary mixture of cis-trans-isomers, were estimated. The decrease in alpha after binding with metal ions is likely caused by the redistribution of the positive charge to benzothiazolium through the conjugated system of 1. Correlations between the decrease in conductivity (decrease in alpha) and the hypsochromic shift Delta lambda(max) after the formation of complexes between 1 and metal ions were observed. [ DOI ]

Photosensitive supramolecular systems based on amphiphilic crown others / S. Y. Zaitsev, V. P. Vereschetin, S. P. Gromov et al. // Supramolecular Science. — 1997. — Vol. 4, no. 3-4. — P. 519–524. An amphiphilic crown-ether styryl dye was synthesized and its properties at the interfaces were investigated. This dye, which in monolayers interacts with some cations and shows reversible changes of the light reflection after photoactivation near the absorption maximum, is an excellent component of functional organized systems. (C) 1997 Elsevier Science Ltd. All rights reserved. [ DOI ]

Structure and ion-complexing properties of an aza-15-crown-5 ether dye: synthesis, crystallography, nmr spectroscopy, spectrophotometry and potentiometry / M. V. Alfimov, A. V. Churakov, Y. V. Fedorov et al. // Journal of the Chemical Society. Perkin Transactions 2. — 1997. — no. 11. — P. 2249–2256. The perchlorate of 2-[2-[4-(13-aza-1,4,7,10-tetroxa-13-cyclopentadecyl)phenyl] ethenyl}-3-ethyl- benzothiazolium (3) has been synthesised and its structure determined in the crystalline state by X-ray diffraction and in solution in acetonitrile by H-1 NMR methods, Complexation with barium and silver cations in solution has been studied in comparison with other model azacrown molecules by spectrophotometric and potentiometric methods. With the exception of the puckered azacrown moiety, the structure of 3 is remarkably planar, consistent with extensive pi-conjugation throughout the remainder of the molecule in both solid and solution states. Compound 3 forms a stable 1:1 complex with Ba2+ ions in acetonitrile, with a stability constant of K-1 = 80 +/- 10 dm(3) mol(-1); the complexation results in major changes in the electronic absorption spectrum of 3, consistent with binding to the azacrown moiety, A model compound, phenylaza-15-crown-5 (2a), was found to bind Ba2+ to form both a I: 1 ligand-metal complex (LM), with a stability constant of K-1 = (2.0 +/- 0.2) x 10(4) dm(3) mol(-1), and a 2:1 (L2M) complex, with a stability constant of K-2 = 220 +/- 20 dm(3) mol(-1) for binding of the second Ligand. The electronic absorption and NMR spectra both indicate binding of the 'hard' Ba2+ cation to the azacrown oxygen atoms, However, by contrast, the evidence from NMR data shows that the 'soft' Ag+ cation complexes with 2a mainly through a strong interaction with the azacrown nitrogen atom, giving a 1 :1 complex with a stability constant of K-1 = 6 +/- 1 dm(3) mol(-1), determined by potentiometry. No complexation of 3 with Ag+ is observed, Studies of the simple aza-15-crown-5 ether reveal strong complexation with both Ba2+(K-1 x K-2 > 10(12)dm(6) mol(-2)) and Ag+ [K-1 = (1.15 +/- 0.10) x 10(4) dm(3) mol(-1) and K-2= 450 +/- 20 dm(3) mol(-1)]. [ DOI ]

Aggregation and photoisomerization of amphiphilic crown-ether styryl dye in monolayers at the interface / E. Y. Kryukov, A. V. Feofanov, V. A. Oleinikov et al. // Russian Chemical Bulletin. — 1996. — Vol. 45, no. 10. — P. 2362–2368. The molecules of trans-isomer of styryl dye la, containing the benzo-18-crown-6 moiety and the methoxybenzothiazole residue with the N-octadecyl substituent, were shown to form stable, highly ordered monolayers at the water/air interface. Increasing the surface pressure of the monolayer results in the formation of the H-aggregated molecules of compound la. The H-aggregates tend to dissociate to the monomeric trans-form, when the monolayer forms in the Langmuir-Blodgett film (LB film). The light irradiation of the LB films leads to the partially reversible trans-cis-photoisomerization of compound la, whose efficiency is much lower than that observed in an acetonitrile solution of In. The aggregation of cis-la isomers in the LB film is suggested to hamper the reverse cis-trans-isomerization. The aggregation of trans-1a molecules in the LB films does not occur in air, but, after dipping in an aqueous solution, molecules of the LB film slowly form J-aggregates. A model of the structural organization of trans-la molecules in the LB films was proposed. [ DOI ]

Crown ether styryl dyes .17. influence of the length of the n-substituent in betaines of chromogenic 15-crown-5-ethers on complexation with cations of alkaline-earth metals / O. B. Stanislavskii, E. N. Ushakov, S. P. Gromov et al. // Russian Chemical Bulletin. — 1996. — Vol. 45, no. 3. — P. 564–572. The stoichiometry of complexation of crown ether styryl dyes with Mg2+, Ca2+, and Ba2+ ions and the dependence of the stability constants of these complexes on the length of the N-sulfoalkyl substituent were investigated. Introduction of a terminal sulfo group into the N-ethyl substituent had but a small effect on the stability constant for the complexes with 1:1 stoichiometry. Increase in the length of the N-substituent by one or two methylene groups resulted in a jumpwise rise of this constant. The effect observed was attributed to the formation of the intramolecular ion pair, The dimerization constant for Mg2+ complexes increased dramatically when passing from the sulfopropyl N-substituent to the sulfobutyl. one. The increase in the constant results from the decrease in steric strains in the dimeric complex. [ DOI ]

Crown ether styryl dyes .18. synthesis, anion-”capped” complexes, and ion-selective stereospecific [2+2] autophotocycloaddition of photochromic 18-crown-6 ethers / S. P. Gromov, E. N. Ushakov, O. A. Fedorova et al. // Russian Chemical Bulletin. — 1996. — Vol. 45, no. 3. — P. 654–661. New crown ether styryl dyes (trans-1c,d) containing the 18-crown-6 ether fragment were synthesized. interaction of trans-1c,d dyes, as well as their analogs, trans-1a,b containing the 15-crown-5 ether fragment, with Ca(ClO4)(2) in MeCN afforded supramolecular structures (dimeric complexes). Competing reactions, trans-cis-photoisomerization with the formation of anion-”capped” complexes of cis-1a-d and [2+2] autophotocycloaddition with the formation of cyclobutane derivatives 8a-d and Be, were observed on photolysis of solutions Elf complexes of trans-1a-d with Ca2+. Preorganization of trans-isomers in dimeric complexes with Ca2+ determined the regio- and stereoselectivity of each of the two directions of the photocycloaddition and the efficiency of the reaction. [ DOI ]

Grs-active substrates based on thin silver films annealed at high temperatures: A comparative study by techniques of atomic-force microscopy and giant raman scattering spectroscopy / S. A. Maskevich, I. F. Sveklo, A. V. Feofanov et al. // Optics and Spectroscopy (English translation of Optika i Spektroskopiya). — 1996. — Vol. 81, no. 1. — P. 95–102.

Gromov S. P., Vedernikov A. I., Fedorova O. A. Macrocycle opening in crown ethers .2. template effect in macrocycle opening in formyl derivatives of benzocrown ethers under the action of amines with the formation of podands // Russian Chemical Bulletin. — 1996. — Vol. 45, no. 3. — P. 648–653. Macrocycle opening in derivatives of benzocrown ethers under the action of amines is affected by the nature of the heteroatoms in the macrocycle, the nature of the functional group in the benzene ring of the crown ether, and the length, branching, and number oi hydrocarbon radicals at the amine nitrogen atom. A distinguishing feature of this reaction is the template effect of MeNH(3)(+), Me(2)NH(2)(+), Na+, and K+ ions. [ DOI ]

Surface-enhanced resonance raman spectra of photochromic crown ether styryl dyes, their model chromophores, and their complexes with mg2+ / A. Feofanov, A. Ianoul, V. Oleinikov et al. // The Journal of physical chemistry. — 1996. — Vol. 100, no. 6. — P. 2154–2160. The complexation of the derivatives of crown ether styryl dyes betaine 2-[2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclop entadecin-16-yl)ethenyl]-3-(3-sulfopropyl)benzothiazolium (1a) and perchlorate 2-[2-(2,3,5,6,8,9,11,12-octahydro-1,4,7, 10,13-benzopentaoxacyclopentadecin-16-yl)ethenyl]-3-ethylbenzothiazolium (1b) and their molecular fragment 2,3,5,6,8,9,11, 12-octahydro-1,4,7, 10,13-benzopentaoxacyclopentadecin (2) with magnesium cations has been studied by the surface-enhanced Raman scattering (SERS) spectroscopy at very low (down to 10(-8) M) concentrations. A detailed comparison of the Raman and SERS spectra of 1a,b and their molecular fragments 2 and perchlorate 2-Me-3-ethyl benzothiazolium (3) enabled one to assign the vibrational modes and propose the model of dye interaction with the silver SERS-active surface. Benzo-15-crown-5 chromophore of la,b was found to be adsorbed through its crown ether part so that the plane of benzene ring is nearly perpendicular to the surface of,silver electrode. The C=C bond as well as the benzothiazolium chromophore being situated far from the electrode surface does not contribute noticeably to the SERS spectra. The sulfonate group of la and alkyl group of 1b do not affect the geometry of adsorption. The SERS spectra of trans-1a,b and their complexes with Mg2+ are observed selectively studying the photostationary mixtures of cis and trans isomers. The complexation of Mg2+ leads to the remarkable frequency shifts of several bands associated primarily with the benzo-15-crown-5 fragment of 1a,b. The spectral effects which reflect the cation-induced intramolecular electron transfer were found to be very similar in both resonance Raman and SERS spectra of the dyes. Hence, the adsorption on the surface of silver electrode does not perturb the complexation of the dyes with Mg2+. The results demonstrate that the SERS spectroscopy enables one to study the complexation of the photochromic crown ether styryl dyes with the metal cations, ensuring selective detection of trans isomers and high sensitivity to structural changes of the dyes in a wide range of concentrations. [ DOI ]

Synthesis and spectroscopic studies of novel photochromic benzodithiacrown ethers and their complexes / M. V. Alfimov, Y. V. Fedorov, O. A. Fedorova et al. // J. Chem. Soc., Perkin Trans. 2. — 1996. — P. 1441–1447. New styryl dyes containing the benzodithia-18-crown-6 fragment have been synthesized and their photoisomerization reactions and complexes with Hg2+ and Ag + cations have been investigated by steady-state electronic and resonance Raman spectroscopy. (4-Formy1benzo)dithia- 18-crown-6,N-carboxypropyl- and N-carboxybutyl-2-methylbenzothiazolium bromides have also been prepared as intermediates for the styryl dye syntheses. Changes in vibrational resonance Raman spectra observed on complexation with Agf and HgZf cations or on variation of solvent polarity have been correlated with changes in the UV-VIS absorption maxima of the dyes. Preliminary assignments of the observed Raman bands to particular vibrations are made. [ DOI ]

FEDOROVA O. A., GROMOV S. P., ALFIMOV M. V. Crown-ether styryl dyes, spectral effects and complexation of chromogenic 15-crown-5 ether by nmr h-1 and uv-spectroscopy // Doklady Akademii nauk SSSR. — 1995. — Vol. 341, no. 2. — P. 219–223.

Crown-containing styryl dyes .13. the nature of the heterocysts moiety, complexation, and electronic absorption and fluorescence-spectra of trans-isomers and cis-isomers of photochromic 15-crown-5-ethers / S. P. Gromov, A. A. Golosov, O. A. Fedorova et al. // Russian Chemical Bulletin. — 1995. — Vol. 44, no. 1. — P. 124–130. New crown ether styryl dyes containing various heterocyclic moieties and substituents were synthesized. The cia and trans isomers of crown ether styryl dyes and their complexes with metal cations were characterized by their absorption and fluorescence spectra. Based on an analysis of the spectral parameters and the shifts of the absorption and fluorescence maxima upon photoisomerization and complexation, the effects of the nature and structure of the heterocyclic moiety on the photochromism of styryl ionophores were revealed. [ DOI ]

Crown-containing styryl dyes .14. synthesis, luminescence, and complexation of the trans-isomers of chromogenic 15-crown-5-ethers / S. P. Gromov, O. A. Fedorova, M. V. Alfimov et al. // Russian Chemical Bulletin. — 1995. — Vol. 44, no. 10. — P. 1922–1928. Novel crown ether styryl dyes containing heterocyclic residues with various substituents were synthesized. The fluorescence and absorption spectra of the trans-isomers of crown ether styryl dyes and their complexes with metal cations were studied. Based on spectral data, the influence of the nature of a heterocyclic residue, the crown ether fragment, and the temperature on the fluorescence of dyes and their complexes with metal cations was elucidated. [ DOI ]

Crown-ether styryl dyes .15. synthesis and two pathways of regio- and stereospecific cation-dependent [2+2]-autophotocycloaddition of chromogenic 15-crown-5-ether betaines of quinoline series / S. P. Gromov, O. A. Fedorova, E. N. Ushakov et al. // Russian Chemical Bulletin. — 1995. — Vol. 44, no. 11. — P. 2131–2136. Styryl dyes (4a,b) containing a 15-crown-5 fragment and isomeric 2- and 4-quinolinium residues with an N-sulfopropyl substituent undergo [2+2] -autophotocycloaddition to give cyclobutane derivatives (9a,b) in acetonitrile only in the presence of Mg(ClO4)(2) or Ca(ClO4)(2). The stereospecificity of both pathways of photocycloaddition and its efficiency are explained by the preorganization of the supramolecular dimers derived from the trans-isomers of the dyes when they are bound into complexes with Mg and Ca cations. [ DOI ]

Crown-ether styryl dyes .16. betaines of photochromic 15-crown-5 ethers and their complexes with mg2+: A surface enhanced raman scattering spectroscopy study / A. V. Feofanov, A. I. Ianoul, V. A. Oleinikov et al. // Russian Chemical Bulletin. — 1995. — Vol. 44, no. 12. — P. 2323–2330. The surface enhanced Raman scattering (SERS) spectra of styryl dyes containing a crown-ether group and a heteroaromatic residue with sulfoalkyl (1a) or alkyl (1b) N-substituent and of their complexes with Mg2+ cations were recorded in the 10(-4)-10(-8) mol L(-1) concentration range. A model for the interaction of compounds 1a,b with a silver surface during their adsorption on an electrochemically treated electrode was suggested. Fast cis-trans relaxation of the adsorbed molecules 1a,b and complexes (1a,bMg2+ was found. It was shown that at [1a] = 10(-5) mol L(-1) and moderate molar ratios (C-Mg/[1a] = 3/1 to 9/1) in acetonitrile solutions, (trans-1aMg2+ complexes are joined into head-to-tail type dimers. An excess of Mg2+ cations (c(Mg)/[1a] > 100) leads to dissociation of the dimers yielding (trans-1a)(Mg2+)(2) complexes. The formation of dimers from complexes (trans-1aMg2+ is accompanied by a substantial distortion of the planar structure of trans-1a. This may be an important factor influencing the efficiency of photocycloaddition involving dimers of (trans-1a) Mg2+. [ DOI ]

Excited state relaxation processes of crowned styryl dyes and their metal complexes / S. I. Druzhinin, M. V. Rusalov, B. M. Uzhinov et al. // PROCEEDINGS OF THE INDIAN ACADEMY OF SCIENCES-CHEMICAL SCIENCES. — 1995. — Vol. 107, no. 6. — P. 721–727. The fluorescence of novel crowned styryl dyes and their complexes with sodium cation was studied. The fluorescence quantum yield of crowned styryl dye is higher than that of non-crowned ones. While absorption and fluorescence spectra of a styryl dye are shifted to high frequency regions, its fluorescence quantum yield in the absence of photoisomerization is practically unchanged, and the rate constant of its temperature fluorescence qienching rises as it forms a complex with the metal ion. The relaxation processes of photoisomerization and recoordination are considered. The adiabatic change of metal ion coordination in crown cycle may proceed in the excited state. The trans-cis photoisomerization of styryl dyes and their metal complexes is a barrierless reaction.

Fluorescence of crown-containing styryl dyes and of their metal complexes / S. I. Druzhinin, M. V. Rusalov, B. M. Uzhinov et al. // Zhurnal Prikladnoi Spektroskopii. — 1995. — Vol. 62, no. 3. — P. 69–72. Fluorescence of the new crown-contg. styryl dyes and their complexes with Na cation was studied. The fluorescence quantum yield of the styryl dye increases during incorporation of the crown-ether substituent. Formation of the complex of crown-ether with a metal ion leads to the short-wave shift of the absorption and fluorescence bands, does not practically affect the fluorescence quantum yield of the dye in the absence of photoisomerization and increases the rate const. of the temp. fluorescence quenching. In the excited state the adiabatic change of the metal ion coordination in crown-cycle is possible. The trans-cis-photoisomerization of the styryl dyes and their metal complexes is a barrierless reaction.

GROMOV S. P., VEDERNIKOV A. I., FEDOROVA O. A. Macrocycle opening in formyl derivatives of benzocrown ethers under the action of methylamine // Russian Chemical Bulletin. — 1995. — Vol. 44, no. 5. — P. 923–926. A new method for synthesizing nitrogen-containing podands by nucleophilic regioselective cleavage of the macrocycle in formyl derivatives of benzocrown ethers by heating with methylamine and methylammonium chloride has been developed. This reaction is the first example of crown ether opening by a nitrogen-containing nucleophile. [ DOI ]

Gromov S., Fedorova O., Alfimov M. Photochromic ionophores: synthesis, photoinduced isomerization and cycloaddition of crown ether styryl dyes // Molecular Crystals and Liquid Crystals. — 1994. — Vol. 246. — P. 183–186. The synthesis and structure of crown ether styryl dyes representing a novel class of dyes are considered. Data on photoisomerization and photoinduced 1,2-cycloaddition with formation of cyclobutane derivative sare briefly analyzed. [ DOI ]

A raman-spectroscopic study of photochromic benzothiazolium dyes / I. K. Lednev, O. A. Fyedorova, S. P. Gromov et al. // Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy. — 1993. — Vol. 49, no. 8. — P. 1055–1063. Resonance Raman spectra using several excitation wavelengths have been obtained in the region 300-1750 cm-1 for two photochromic benzothiazolium dyes containing a crown ether ring. Bands arising from both cis- and trans-isomers have been distinguished by comparing the spectra observed at different resonances and under different sample conditions. Preliminary assignments of the bands have been made, allowing insight into the changes in structure and bonding which occur on photoisomerization. [ DOI ]

Crown-containing styryl dyes .8. cation-dependent concerted [2+2]-autophotocycloaddition of photochromic 15-crown-5 ether betaines / M. V. Alfimov, S. P. Gromov, O. B. Stanislavskii et al. // Russian Chemical Bulletin. — 1993. — Vol. 42, no. 8. — P. 1385–1389. Styryl dyes containing a crown ether group and a heteroaromatic moiety with a sulfoalkyl N-substituent (1a,b) undergo photocyclodimerization in acetonitrile in the presence of Mg(ClO4)2 to give only the type A isomer of cyclobutane derivative (2a,b). The photochemical regio- and stereoselectivity of the cycloaddition is explained by self-organization of the trans-isomers of the styryl dyes upon complexation with the Mg2+ cations into dimers with a fixed mutual arrangement of multiple bonds. [ DOI ]

Novel synthesis of benzocrown ethers formylated in the benzene-ring / S. P. Gromov, O. A. Fedorova, A. I. Vedernikov et al. // Russian Chemical Bulletin. — 1993. — Vol. 42, no. 5. — P. 960–961. [ DOI ]

Crown-ether styryl dyes .6. photoinduced and dark cation-dependent dimerization of photochromic 15-crown-5-ether betaines / Y. N. Ushakov, O. B. Stanislavskii, S. P. Gromov et al. // Doklady Akademii nauk SSSR. — 1992. — Vol. 323, no. 4. — P. 702–706.

Crystal and molecular-structure of the iodide salt of a new chromogenic 15-crown-5-ether / V. V. Tkachev, L. O. Atovmyan, S. P. Gromov et al. // Journal of Structural Chemistry. — 1992. — Vol. 33, no. 4. — P. 588–595. We have investigated the spatial structure of the first representative of a chromogenic crown ether of the styrene series: the iodide salt of chromogenic 15-crown-5-ether. Isometrically shaped sample with 0.4 mm cross section; 3683 independent nonzero reflections (I > 3sigma(I)); KM-4 diffractometer; CuKalpha radiation; C27H35O6,5NIS; a = 10.793(1), b = 10.591 1), c = 14.763(3) angstrom, alpha = 97.44(1), beta = 119.23(2), gamma = 72.86(1)-degrees; V = 1407.0(3) angstrom3;M = 636.6; d(calc) 1.496 g/cm3 for Z = 2, space group P1BAR; direct method, least-squares refinement in the anisotropic approximation (isotropic for the hydrogen atoms), DIFABS correction for absorption, R = 3.6%. We show that in the single crystal, one-half an ethanol molecule corresponds to each salt. The styrene dye has a planar structure. In the macrocycle, in the C(sp2)OCC units both torsional angles have the same sign; the oxygen atoms of these units are rotated toward different sides of the plane of the entire molecule. The COCCOC units in one case have a gauche-gauche-gauche conformation and in the other case have a trans-trans-gauche conformation, which have not encountered previously in benzo-15-crown-5 and its analogs. Such a rearrangement of the macrocycle leads to reorientation of the unshared electron pairs of the rest of the oxygen atoms out of the plane of the macrocycle.

Dependence of metal-ion complexation and intermolecular aggregation on photoinduced geometric isomerism in a crown-ether styryl dye / A. V. Barzykin, M. A. Fox, E. N. Ushakov et al. // Journal of the American Chemical Society. — 1992. — Vol. 114, no. 16. — P. 6381–6385. Photoisomerization and complexation with alkaline-earth metal cations of a 2-[2-(2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-16-yl)ethenyl]-3-(3-sulfopropyl)benzothiazolium betaine has been studied by steady-state and time-resolved electronic spectroscopy. The dye is highly sensitive to complexed metal cations, showing characteristic hypsochromic shifts of the long wavelength absorption and fluorescence bands, as well as a decrease in the fluorescence quantum yield upon complexation. The stabilities of the complexes are drastically changed by photoisomerization, with enhanced stability of the cis ligand complex being attributed to the intramolecular interaction of the complexed cation with a tethered sulfonate anion. This intramolecular capping also induces a strong hypsochromic shift of up to 70 nm from the absorption maximum of the uncapped trans ligand complex. Unlike this capped cis complex, the uncapped trans complex is partially aggregated, even at low concentration, as a result of the association of the sulfonate anion of one dye with the "crowned' cation of a second molecule. At high metal ion concentrations, the aggregates dissociate as the sulfonate group becomes associated with a free metal cation. Similar interactions are also responsible for the relaxation of the anion-capped cis complex to its "uncapped" form at high cation concentrations. [ DOI ]

Crown-ether styryl dyes - size of chelate macrocycle and complexation of cis-isomers of photochromic 15-crown-5 ether betaines / S. P. Gromov, O. A. Fedorova, Y. N. Ushakov et al. // Doklady Akademii nauk SSSR. — 1991. — Vol. 321, no. 1. — P. 104–107.

Crown-ether styryl dyes .2. synthesis, photoinduced and dark complexation of chromogenic 15-crown-5-ether betaine / S. P. Gromov, O. A. Fedorova, Y. N. Ushakov et al. // Doklady Akademii nauk SSSR. — 1991. — Vol. 317, no. 5. — P. 1134–1139.

Crown-ether styryl dyes .3. synthesis and x-ray crystal analysis of chromogenic 15-crown-5 ether / S. P. Gromov, O. A. Fedorova, M. V. Alfimov et al. // Doklady Akademii nauk SSSR. — 1991. — Vol. 319, no. 5. — P. 1141–1144.

Picosecond isomerization of crown-containing styryl dyes in excited electron state / M. V. Alfimov, O. E. Buyevich, S. P. Gromov et al. // Doklady Akademii nauk SSSR. — 1991. — Vol. 319, no. 5. — P. 1149–1154.

Palladium(ii)-coproporphyrin-i as a photoactivable group in sequence-specific modification of nucleic-acids by oligonucleotide derivatives / O. FEDOROVA, A. SAVITSKII, K. SHOIKHET, G. PONOMAREV // FEBS Letters. — 1990. — Vol. 259, no. 2. — P. 335–337. 10.1016/0014-5793(90)80041-G.

Kovalev V. V., Fedorova O. A., Shokova E. A. Synthesis of 1-(1-arylalkyl)adamantanes // ZHURNAL ORGANICHESKOI KHIMII. — 1987. — Vol. 23, no. 11. — P. 2396–2399.

Показать все