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1.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Lavrinchenko I. A., Moseev T. D., Varaksin M. V., Zyryanov G. V., Taniya O. S., Tsmokalyuk A. N., Charushin V. N., Chupakhin O. N., Demidov O. P., Borovlev I. V.
Заглавие : A BF3-mediated C–H/C–Li coupling of 1,3,7-triazapyrene with 2-thienyllithium in the design of push–pull fluorophores and chemosensors for nitroaromatics
Место публикации : New Journal of Chemistry. - 2022. - Vol. 46, № 11. - С. 5121-5128
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Mono- and bis-2-thienyl-substituted 1,3,7-triazapyrenes have been synthesized for the first time via BF3-mediated C–H/C–Li coupling of 1,3,7-triazapyrene with 2-thienyllithium in 33 and 51% yields, respectively. The photophysical properties of these polycyclic azaaromatics have been studied, with emission in the range of 450–500 nm and fluorescence quantum yields of up to 99% in methanol solutions being revealed. The turn-off chemosensing properties of 2-thienyl-substituted 1,3,7-triazapyrenes for the selective detection of nitroaromatics have also been assessed; in particular, the quenching constants according to the Stern–Volmer model, the quenching sphere radius according to the Perrin model, the detection limit and the quenching efficiency have been determined. In particular, 6,8-bis-(thiopen-2-yl)-1,3,7-triazapyrene, characterized by 10 times the quenching constant and limit of detection (LOD) compared to the mono-substituted analog, can be considered as the most promising chemosensor for determining nitroaromatic compounds. DFT calculations confirm the presence of intramolecular charge transfer (ICT) effects in the case of the obtained fluorophores and clarify the quenching mechanism for nitroaromatics.
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2.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Moseev T. D., Varaksin M. V., Virlova E. A., Medvedeva M. V., Svalova T. S., Melekhin V. V., Tsmokalyuk A. N., Kozitsina A. N., Charushin V. N., Chupakhin O. N.
Заглавие : Fluoroaromatic 2H-imidazole-based push-pull fluorophores: Synthesis, theoretical studies, and application opportunities as probes for sensing the pH in saliva
Место публикации : Dyes and Pigments. - 2022. - Vol. 202. - Ст.110251
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
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3.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Slovesnova N. V., Minin A. S., Taniya O. S., Tsmokalyuk A. N., Kovalev I. S., Kopchuk D. S., Krinochkin A. P., Zyryanov G. V., Charushin V. N., Petrov A. Y., Kim G. A., Smolyuk L. T., Pozdina V. A.
Заглавие : Synthesis of new water-soluble polyarene-substituted naphtho[1,2-d]oxazole-based fluorophores as fluorescent dyes and biological photosensitizers
Место публикации : Dyes and Pigments. - 2022. - Vol. 204. - Ст.110410
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
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4.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Taniya O. S., Fedotov V. V., Sadieva L. K., Krinochkin A. P., Kovalev I. S., Kopchuk D. S., Zyryanov G. V., Ulomsky E. N., Rusinov V. L., Charushin V. N., Novikov A. S., Liu Y.
Заглавие : Abnormal push-pull benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidine fluorophores in planarized intramolecular charge transfer (PLICT) state: Synthesis, photophysical studies and theoretical calculations
Место публикации : Dyes and Pigments. - 2022. - Vol. 204. - Ст.110405
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: The combination of excellent luminescence with high solvent polarity effect and aggregation induced emission (AIE) is an ideal combination for creating fluorophores/probes with high microenvironmental sensitivity. However, many push-pull chromophores of the D−A type in common intramolecular charge transfer (ICT) state with a significant solvatochromic effect and AIE activity, have poor luminescent properties. Herein, to overcome this problem by using reactions of nucleophilic aromatic hydrogen substitution (SNH), we have designed a series of novel 4-heteroaryl-substituted 2-aryl-2H-benzo[4,5]imidazo[1,2-a][1,2,3]triazolo[4,5-e]pyrimidine fluorophores possessing a planarized intramolecular charge transfer (PLICT) state. All these fluorophores exhibited high luminescence quantum yields (up to 60%) and large Stokes shift values of up to 7459 cm−1. Among them, the fluorophore 4h was found to exhibit the most pronounced positive solvatochromic effect and the probe 4f exhibited the most pronounced aggregation induced emission characteristics. This AIE behavior was further confirmed by means of time-resolved fluorescence lifetime measurements as well as DFT-assisted geometry optimization studies. In the presence of trifluoroacetic acid (TFA) compound 4h exhibited a well-pronounced acidochromism via visible color change from yellow-green to orange which returned to the original yellow-green solution after the addition of triethylamine (TEA). The Stern-Volmer constant for the probe 4h towards TFA was 38 M−1. Finally, for the compounds 4f, g, h theoretical calculations in the ground and excited states in different solvents were carried out to confirm the PLICT process. Based on all above the herein reported PLICT fluorophores 4a-h can be successfully applied as biological probes and optical switches.
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5.

Вид документа : Статья из сборника (однотомник)
Шифр издания :
Автор(ы) : Lavrinchenko I. A., Moseev T. D., Seleznev Y. A., Varaksin M. V., Charushin V. N., Chupakhin O. N.
Заглавие : Design and synthesis of y-shaped fluorophores based on n(2)-aryl-1,2,3 triazoles
Место публикации : Успехи синтеза и комплексообразования = Advances in synthesis and complexing : сборник тезисов шестой Международной научной конференции. - Москва, 2022. - С. 240
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
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6.

Вид документа : Статья из сборника (однотомник)
Шифр издания :
Автор(ы) : Lavrinchenko I. A., Moseev T. D., Seleznev Y. A., Varaksin M. V., Charushin V. N., Chupakhin O. N.
Заглавие : An efficient synthesis of push-pull fluorophores based on (2-fluoroaryl)-1,2,3-triazoles
Место публикации : Успехи синтеза и комплексообразования = Advances in synthesis and complexing : сборник тезисов шестой Международной научной конференции. - Москва, 2022. - С. 194
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
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7.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Moseev T. D., Nikiforov E. A., Varaksin M. V., Starnovskaya E. S., Savchuk M. I., Nikonov I. L., Kopchuk D. S., Zyryanov G. V., Chupakhin O. N., Charushin V. N.
Заглавие : Novel pentafluorophenyl- and alkoxyphenyl-appended 2,2'-bipyridine push-pull fluorophores: a convenient synthesis and photophysical studies
Место публикации : Synthesis. - 2021. - Vol. 53, № 19. - С. 3597-3607
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Ключевые слова (''Своб.индексиров.''): 2,2′-bipyridines--1,2,4-triazines--polyfluoroarenes
Аннотация: A convenient method for the synthesis of new highly in non-polar solvents soluble photoactive pentafluorophenyl-substituted and extended alkoxyphenyl-substituted 2,2′-bipyridines is reported. The synthetic strategy for the preparation of such ligands involves a sequence of several structural transformations, such as O-alkylation, nucleophilic substitution of hydrogen (SN H) in 1,2,4-triazine precursors via the ‘addition–elimination’ scheme, and the subsequent conversion of the obtained 1,2,4-triazines into 2,2′-bipyridines by means of the aza-Diels–Alder reaction. The photophysical properties of the synthesized novel pentafluoroaryl-substituted 2,2′-bipyridines were comprehensively studied. The obtained photophysical data indicate the competitive advantages of the herein reported pentafluoroarylated push–pull fluorophores, bearing extended aliphatic moieties, over their analogues containing benzoxy or phenolic fragments in terms of improvement in quantum yield and well-pronounced positive solvatochromism confirmed by the mathematical analysis according to the Lippert–Mataga equation.
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8.

Вид документа : Статья из журнала
Шифр издания :
Автор(ы) : Smyshliaeva L. A., Varaksin M. V., Fomina E. I., Medvedeva M. V., Svalova T. S., Kozitsina A. N., Charushin V. N., Chupakhin O. N., Demidov O. P., Borovlev I. V., Mensch C., Mampuys P., Maes B. U. W.
Заглавие : 1,3,7-triazapyrene-based ortho-carborane fluorophores: convenient synthesis, theoretical studies, and aggregation-induced emission properties
Место публикации : Organometallics. - 2021. - Vol. 40, № 16. - С. 2792-2807
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: A convenient transition-metal-free approach, based on nucleophilic substitution of hydrogen (SNH), for consecutive regioselective C–H functionalization of 1,3,7-triazapyrene scaffolds with carboranyllithium and phenyllithium is reported. The theoretical calculations disclosed highlight key features in the regioselectivity and mechanism of the investigated SNH transformations. The novel 1,3,7-triazapyrene-based ortho-carboranes obtained have large potential in the field of molecular electronics as organic luminophores, which are characterized by the aggregation-induced emission and dual-emission effects.
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9.

Вид документа : Статья из журнала
Шифр издания : Г/A 99
Автор(ы) : Taniya O. S., Khasanov A. F., Varaksin M. V., Starnovskaya E. S., Krinochkin A. P., Savchuk M. I., Kopchuk D. S., Kovalev I. S., Nosova E. V., Zyryanov G. V., Chupakhin O. N., Kim G. A.
Заглавие : Azapyrene-based fluorophores: synthesis and photophysical properties
Место публикации : New Journal of Chemistry. - 2021. - Vol. 45, № 45. - С. 20955-20971
ББК : Г
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
Аннотация: Azapyrenes are the nitrogen isosteres of pyrene. Based on theoretical and experimental studies, electron–acceptor azapyrene domains may be considered as convenient scaffolds for constructing a large variety of “push–pull” π-conjugated chromophores with pronounced ICT properties. Over the past decade, due to the unrelenting interest in functional materials and modern methodologies such as cross-coupling, peri-annulation, direct C–H-functionalization, etc., methods for the synthesis of aryl(alkyl) K-functionalized azapyrenes and other derivatives have been developed, and their photophysical and electrochemical properties have been studied. This short review aims at critical analysis of the best known/modern methods for the preparation of functionalized azapyrene derivatives, as well as an assessment of their photophysical/electrochemical properties in comparison with the structural and electronic properties of the parent pyrene.
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10.

Вид документа : Статья из сборника (однотомник)
Шифр издания :
Автор(ы) : Moshkina T. N., Kopotilova A. E., Nosova E. V., Lipunova G. N., Charushin V. N.
Заглавие : Synthesis of “push-pull” fluorophores based on 2-aryl(heteryl)quinazolines
Место публикации : Mendeleev 2021: book of abstracts XII international conference on chemistry for young scientists. - Saint Petersburg, 2021. - С. 607
Предметные рубрики: ХИМИЧЕСКИЕ НАУКИ
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