Isoxazolyl-Derived 1,4-Dihydroazolo[5,1-c][1,2,4]Triazines: Synthesis and Photochemical Properties
Электронный научный архив УРФУ
Информация об архиве | Просмотр оригинала| Поле | Значение | |
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Isoxazolyl-Derived 1,4-Dihydroazolo[5,1-c][1,2,4]Triazines: Synthesis and Photochemical Properties
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| Автор |
Sadchikova, E. V.
Safronov, N. E. Beliaev, N. A. Nenajdenko, V. G. Belskaya, N. P. |
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| Тематика |
AIE EFFECT
DIAZOIMIDAZOLE DIAZOPYRAZOLE DIHYDROAZOLO[5,1-C][1,2,4]TRIAZINES ENAMINE FLUORESCENCE ISOXAZOLE SOLVATOCHROMISM |
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| Описание |
New fluorescent dyes containing an assembled 1,4-dihydroazolo[5,1-c][1,2,4]triazine (DAT) core and an isoxazole ring were synthesized through a reaction between diazopyrazole or diazoimidazoles and isoxazolyl-derived enamines in mild conditions. The photophysical characteristics (maxima absorption and emission, Stokes shifts, fluorescent quantum yields, and fluorescence lifetimes) of the new fluorophores were obtained. The prepared DATs demonstrated emission maxima ranging within 433–487 nm, quantum yields within 6.1–33.3%, and a large Stokes shift. The photophysical characteristics of representative DAT examples were studied in ten different solvents. Specific (hydrogen bonds) and non-specific (dipole–dipole) intermolecular and intramolecular interactions were analyzed using XRD data and spectral experiments. Solvatochromism was analyzed using Lippert–Mataga and Dimroth–Reichardt plots, revealing the relationship between the DAT structure and the nature of solute–solvent interactions. The significant advantages of DATs are the fluorescence of their powders (QY up to 98.7%). DAT-NMe2 10 expressed bright aggregation-induced emission (AIE) behavior in DMSO and THF as the water content increased. The numerous possible variations of the structures of the heterocycles included in the DATs, as well as substituents, create excellent prospects for adjusting their photophysical and physicochemical properties. © 2023 by the authors.
Ministry of Education and Science of the Russian Federation, Minobrnauka; Ural Federal University, UrFU This research was funded by the Ministry of Science and Higher Education of the Russian Federation (Ural Federal University Program of Development within the Priority 2030 Program). The authors acknowledge partial support from Ural Federal University. |
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| Дата |
2024-04-05T16:19:12Z
2024-04-05T16:19:12Z 2023 |
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| Тип |
Article
Journal article (info:eu-repo/semantics/article) |info:eu-repo/semantics/publishedVersion |
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| Идентификатор |
Sadchikova, EV, Safronov, NE, Beliaev, NA, Nenajdenko, VG & Belskaya, NP 2023, 'Isoxazolyl-Derived 1,4-Dihydroazolo[5,1-c][1,2,4]Triazines: Synthesis and Photochemical Properties', Molecules, Том. 28, № 7, 3192. https://doi.org/10.3390/molecules28073192
Sadchikova, E. V., Safronov, N. E., Beliaev, N. A., Nenajdenko, V. G., & Belskaya, N. P. (2023). Isoxazolyl-Derived 1,4-Dihydroazolo[5,1-c][1,2,4]Triazines: Synthesis and Photochemical Properties. Molecules, 28(7), [3192]. https://doi.org/10.3390/molecules28073192 1420-3049 Final All Open Access, Gold, Green https://www.scopus.com/inward/record.uri?eid=2-s2.0-85152355537&doi=10.3390%2fmolecules28073192&partnerID=40&md5=2d904e295c41c9d908ab6399054bfb70 https://www.mdpi.com/1420-3049/28/7/3192/pdf?version=1680579793 http://elar.urfu.ru/handle/10995/130379 10.3390/molecules28073192 85152355537 |
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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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MDPI
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| Источник |
Molecules
Molecules |
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