Open Access
Molecules, volume 27, issue 22, pages 8029
4-(Aryl)-Benzo[4,5]imidazo[1,2-a]pyrimidine-3-Carbonitrile-Based Fluorophores: Povarov Reaction-Based Synthesis, Photophysical Studies, and DFT Calculations
Publication type: Journal Article
Publication date: 2022-11-19
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
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.
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Fedotov V. V. et al. 4-(Aryl)-Benzo[4,5]imidazo[1,2-a]pyrimidine-3-Carbonitrile-Based Fluorophores: Povarov Reaction-Based Synthesis, Photophysical Studies, and DFT Calculations // Molecules. 2022. Vol. 27. No. 22. p. 8029.
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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. 4-(Aryl)-Benzo[4,5]imidazo[1,2-a]pyrimidine-3-Carbonitrile-Based Fluorophores: Povarov Reaction-Based Synthesis, Photophysical Studies, and DFT Calculations // Molecules. 2022. Vol. 27. No. 22. p. 8029.
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TY - JOUR
DO - 10.3390/molecules27228029
UR - https://doi.org/10.3390/molecules27228029
TI - 4-(Aryl)-Benzo[4,5]imidazo[1,2-a]pyrimidine-3-Carbonitrile-Based Fluorophores: Povarov Reaction-Based Synthesis, Photophysical Studies, and DFT Calculations
T2 - Molecules
AU - Fedotov, Victor V
AU - Valieva, Maria I
AU - Taniya, Olga S
AU - Aminov, Semen V
AU - Kharitonov, Mikhail A
AU - Novikov, Alexander S.
AU - Kopchuk, Dmitry S.
AU - Slepukhin, Pavel A.
AU - Zyryanov, Grigory V.
AU - Ulomsky, Evgeny N
AU - Rusinov, Vladimir L.
AU - Charushin, Valery
PY - 2022
DA - 2022/11/19 00:00:00
PB - Multidisciplinary Digital Publishing Institute (MDPI)
SP - 8029
IS - 22
VL - 27
SN - 1420-3049
SN - 1420-3049
ER -
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@article{2022_Fedotov,
author = {Victor V Fedotov and Maria I Valieva and Olga S Taniya and Semen V Aminov and Mikhail A Kharitonov and Alexander S. Novikov and Dmitry S. Kopchuk and Pavel A. Slepukhin and Grigory V. Zyryanov and Evgeny N Ulomsky and Vladimir L. Rusinov and Valery Charushin},
title = {4-(Aryl)-Benzo[4,5]imidazo[1,2-a]pyrimidine-3-Carbonitrile-Based Fluorophores: Povarov Reaction-Based Synthesis, Photophysical Studies, and DFT Calculations},
journal = {Molecules},
year = {2022},
volume = {27},
publisher = {Multidisciplinary Digital Publishing Institute (MDPI)},
month = {nov},
url = {https://doi.org/10.3390/molecules27228029},
number = {22},
pages = {8029},
doi = {10.3390/molecules27228029}
}
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Fedotov, Victor V., et al. “4-(Aryl)-Benzo[4,5]imidazo[1,2-a]pyrimidine-3-Carbonitrile-Based Fluorophores: Povarov Reaction-Based Synthesis, Photophysical Studies, and DFT Calculations.” Molecules, vol. 27, no. 22, Nov. 2022, p. 8029. https://doi.org/10.3390/molecules27228029.
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