Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
4-(Aryl)-Benzo[4,5]imidazo[1,2-a]pyrimidine-3-Carbonitrile-Based Fluorophores : Povarov Reaction-Based Synthesis, Photophysical Studies, and DFT Calculations. / Fedotov, Victor V; Valieva, Maria I; Taniya, Olga S; Aminov, Semen V; Kharitonov, Mikhail A; Novikov, Alexander S; Kopchuk, Dmitry S; Slepukhin, Pavel A; Zyryanov, Grigory V; Ulomsky, Evgeny N; Rusinov, Vladimir L; Charushin, Valery N.
в: Molecules (Basel, Switzerland), Том 27, № 22, 8029, 19.11.2022.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - 4-(Aryl)-Benzo[4,5]imidazo[1,2-a]pyrimidine-3-Carbonitrile-Based Fluorophores
T2 - Povarov Reaction-Based Synthesis, Photophysical Studies, and DFT Calculations
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 N
N1 - 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. 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, 27, 8029. https://doi.org/10.3390/molecules27228029
PY - 2022/11/19
Y1 - 2022/11/19
N2 - 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.
AB - 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.
KW - Density Functional Theory
KW - Pyrimidines/chemistry
KW - Fluorescent Dyes/chemistry
KW - Ionophores
KW - Magnetic Resonance Spectroscopy
U2 - 10.3390/molecules27228029
DO - 10.3390/molecules27228029
M3 - Article
C2 - 36432130
VL - 27
JO - Molecules
JF - Molecules
SN - 1420-3049
IS - 22
M1 - 8029
ER -
ID: 103128457