4-(Aryl)-Benzo[4,5]imidazo[1,2-a]pyrimidine-3-Carbonitrile-Based Fluorophores: Povarov Reaction-Based Synthesis, Photophysical Studies, and DFT Calculations
Электронный научный архив УРФУ
Информация об архиве | Просмотр оригинала| Поле | Значение | |
| Заглавие |
4-(Aryl)-Benzo[4,5]imidazo[1,2-a]pyrimidine-3-Carbonitrile-Based Fluorophores: Povarov Reaction-Based Synthesis, Photophysical Studies, and DFT Calculations
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| Автор |
Fedotov, V. V.
Valieva, M. I. Taniya, O. S. Aminov, S. V. Kharitonov, M. A. Novikov, A. S. Kopchuk, D. S. Slepukhin, P. A. Zyryanov, G. V. Ulomsky, E. N. Rusinov, V. L. Charushin, V. N. |
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| Тематика |
AGGREGATION-INDUCED EMISSION
AZA-DIELS–ALDER REACTION BENZIMIDAZOLE FLUORESCENCE MECHANOCHROMIC PROPERTIES OXIDATION POVAROV REACTION PYRIMIDINE DENSITY FUNCTIONAL THEORY FLUORESCENT DYES IONOPHORES MAGNETIC RESONANCE SPECTROSCOPY PYRIMIDINES FLUORESCENT DYE IONOPHORE PYRIMIDINE PYRIMIDINE DERIVATIVE CHEMISTRY DENSITY FUNCTIONAL THEORY NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY |
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| Описание |
A series of novel 4-(aryl)-benzo[4,5]imidazo[1,2-a]pyrimidine-3-carbonitriles were obtained through the Povarov (aza-Diels–Alder) and oxidation reactions, starting from benzimidazole-2-arylimines. Based on the literature data and X-ray diffraction analysis, it was discovered that during the Povarov reaction, [1,3] sigmatropic rearrangement leading to dihydrobenzimidazo[1,2-a]pyrimidines took place. The structures of all the obtained compounds were confirmed based on the data from 1H- and 13C-NMR spectroscopy, IR spectroscopy, and elemental analysis. For all the obtained compounds, their photophysical properties were studied. In all the cases, a positive emission solvatochromism with Stokes shifts from 120 to 180 nm was recorded. Aggregation-Induced Emission (AIE) has been illustrated for compound 6c using different water fractions (fw) in THF. The compounds 6c and 6f demonstrated changes in emission maxima or/and intensities after mechanical stimulation. © 2022 by the authors.
Ministry of Education and Science of the Russian Federation, Minobrnauka The research funding from the Ministry of Science and Higher Education of the Russian Federation (Ural Federal University Program of Development within the Priority-2030 Program) is gratefully acknowledged. |
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| Дата |
2024-04-08T11:06:39Z
2024-04-08T11:06:39Z 2022 |
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| Тип |
Article
Journal article (info:eu-repo/semantics/article) Published version (info:eu-repo/semantics/publishedVersion) |
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| Идентификатор |
Fedotov, VV, Valieva, MI, Taniya, OS, Aminov, SV, Kharitonov, MA, Novikov, AS, Kopchuk, DS, Slepukhin, PA, Zyryanov, GV, Ulomsky, EN, Rusinov, VL & Charushin, VN 2022, '4-(Aryl)-Benzo[4,5]imidazo[1,2-a]pyrimidine-3-Carbonitrile-Based Fluorophores: Povarov Reaction-Based Synthesis, Photophysical Studies, and DFT Calculations', Molecules, Том. 27, № 22, 8029. https://doi.org/10.3390/molecules27228029
Fedotov, V. V., Valieva, M. I., Taniya, O. S., Aminov, S. V., Kharitonov, M. A., Novikov, A. S., Kopchuk, D. S., Slepukhin, P. A., Zyryanov, G. V., Ulomsky, E. N., Rusinov, V. L., & Charushin, V. N. (2022). 4-(Aryl)-Benzo[4,5]imidazo[1,2-a]pyrimidine-3-Carbonitrile-Based Fluorophores: Povarov Reaction-Based Synthesis, Photophysical Studies, and DFT Calculations. Molecules, 27(22), [8029]. https://doi.org/10.3390/molecules27228029 1420-3049 Final All Open Access; Gold Open Access; Green Open Access https://www.mdpi.com/1420-3049/27/22/8029/pdf?version=1669270984 https://www.mdpi.com/1420-3049/27/22/8029/pdf?version=1669270984 http://elar.urfu.ru/handle/10995/131328 10.3390/molecules27228029 85142642040 000887420700001 |
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| Язык |
en
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| Права |
Open access (info:eu-repo/semantics/openAccess)
cc-by https://creativecommons.org/licenses/by/4.0/ |
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| Формат |
application/pdf
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| Издатель |
MDPI
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| Источник |
Molecules
Molecules |
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