Push-Pull Structures Based on 2-Aryl/thienyl Substituted Quinazolin-4(3H)-ones and 4-Cyanoquinazolines
Электронный научный архив УРФУ
Информация об архиве | Просмотр оригинала| Поле | Значение | |
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Push-Pull Structures Based on 2-Aryl/thienyl Substituted Quinazolin-4(3H)-ones and 4-Cyanoquinazolines
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| Автор |
Moshkina, T. N.
Nosova, E. V. Permyakova, J. V. Lipunova, G. N. Zhilina, E. F. Kim, G. A. Slepukhin, P. A. Charushin, V. N. |
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| Тематика |
2-(BIPHENYL)QUINAZOLINE
2-THIENYLQUINAZOLINE 4-CYANOQUINAZOLINE DONOR–ACCEPTOR SYSTEMS FLUORESCENCE QUINAZOLIN-4(3H)-ONE Π-LINKER ELECTRONS POWDERS SOLVENTS SPECTROMETRY, FLUORESCENCE TOLUENE SOLVENT TOLUENE ELECTRON POWDER SPECTROFLUOROMETRY |
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| Описание |
Design and synthesis of 2-(aryl/thiophen-2-yl)quinazolin-4(3H)-ones and 4-cyano-2-arylquinazolines with Et2N-, Ph2N- or carbazol-9-yl- electron donating fragment are described. The key photophysical properties of these compounds have been studied by UV/Vis absorption and fluorescence spectroscopy in solvents of different polarity (toluene and MeCN). 2-(Aryl/thiophen-2-yl)quinazolin-4(3H)-ones show fluorescence in blue-green region in toluene solution with quantum yields up to 89% in the case of 2-(4’-N,N-diphenylamino[1,1’-biphenyl]-4-yl)-quinazolin-4(3H)-one. Moreover, triphenylamino derivative based on quinazolin-4(3H)-one with para-phenylene linker displays the highest quantum yield of 40% in powder. The fluorescence QY of Et2N and Ph2N derivatives decrease when going from toluene to MeCN solution, whereas carbazol-9-yl counterparts demonstrate strengthening of intensity that emphasizes the strong influence of donor fragment nature on photophysical properties. 4-Cyanoquinazolines are less emissive in both solvents, as well as, in solid state. The introduction of cyano group into position 4 leads to orange/red colored powder and dual emission bands. Some molecules demonstrate the increase in emission intensity upon addition of water to MeCN solution. According to frontier molecular orbitals (HOMO, LUMO) calculations, the energy gap of 4-cyanoquinazoline decreases by more than 1 eV compared to quinazolin-4-one, that is consistent with experimental data. © 2022 by the authors.
Russian Science Foundation, RSF, (22-23-00006) This research was funded by Russian Science Foundation (grant number No. 22-23-00006), https://rscf.ru/project/22-23-00006/ (accessed on 11 January 2022). |
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| Дата |
2024-04-08T11:06:37Z
2024-04-08T11:06:37Z 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 |
Moshkina, TN, Nosova, EV, Permyakova, JV, Lipunova, GN, Zhilina, EF, Kim, GA, Slepukhin, PA & Charushin, VN 2022, 'Push-Pull Structures Based on 2-Aryl/thienyl Substituted Quinazolin-4(3H)-ones and 4-Cyanoquinazolines', Molecules, Том. 27, № 21, 7156. https://doi.org/10.3390/molecules27217156
Moshkina, T. N., Nosova, E. V., Permyakova, J. V., Lipunova, G. N., Zhilina, E. F., Kim, G. A., Slepukhin, P. A., & Charushin, V. N. (2022). Push-Pull Structures Based on 2-Aryl/thienyl Substituted Quinazolin-4(3H)-ones and 4-Cyanoquinazolines. Molecules, 27(21), [7156]. https://doi.org/10.3390/molecules27217156 1420-3049 Final All Open Access; Gold Open Access; Green Open Access https://www.mdpi.com/1420-3049/27/21/7156/pdf?version=1666749298 https://www.mdpi.com/1420-3049/27/21/7156/pdf?version=1666749298 http://elar.urfu.ru/handle/10995/131323 10.3390/molecules27217156 85141581884 000881586100001 |
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| Язык |
en
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| Связанные ресурсы |
info:eu-repo/grantAgreement/RSF//22-23-00006
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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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MDPI
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| Источник |
Molecules
Molecules |
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