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4‐Heteryl‐Vinyl‐Butenolides as Visible‐Light T‐Type Photoswitches Quantified by Light‐Emitting Diode Nuclear Magnetic Resonance Spectroscopy Научная публикация

Журнал ChemPhotoChem
ISSN: 2367-0932
Вых. Данные Год: 2026, Том: 10, Номер: 9, Номер статьи : e70294, Страниц : DOI: 10.1002/cptc.70294
Авторы Shahkhatuni Aleksan G. 1 , Shahkhatuni Aleksan G. 1 , Petrosyan Sofi A. 1 , Davinyan Andranik M. 1 , Melikyan Gagik S. 2 , Shahkhatuni Astghik A. 1 , Shahkhatuni Astghik A. 1 , Ananikov Valentine P. 3
Организации
1 Scientific Technological Center of Organic and Pharmaceutical Chemistry Yerevan Armenia
2 Yerevan State University Yerevan Armenia
3 N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences Moscow Russia

Реферат: We introduce 4-heteryl-vinyl-butenolides as a new and readily accessible family of T-type molecular photoswitches that combine visible-light addressability with high photostationary-state (PSS) selectivity and tunable thermal stability of the metastable isomer. A series of derivatives was synthesized and evaluated by UV-Vis spectroscopy and in situ light-emitting diode nuclear magnetic resonance spectroscopy (LED-NMR), enabling direct quantification of E/Z ratios and thermal Z → E back-isomerization kinetics in solution. All compounds undergo efficient E →  Z photoisomerization under LED irradiation in the 365–470 nm range, reaching high Z enrichment at PSS (up to 95%–96%) for the best-performing derivatives. The thermal lifetimes of the Z-isomer are readily tuned by substituent electronics and solvent, spanning t1/2 ≈ 1–40 h (with rate constants down to ~10−6 s−1), thus providing a practical balance between photoaddressability and kinetic stability. Importantly, repeated switching is reproducible under ambient conditions and proceeds with minimal side reactions for the majority of the series. These results establish 4-heteryl-vinyl-butenolides as a versatile, designable photoswitch platform for photochemical control in functional materials and molecular systems.
Библиографическая ссылка: Shahkhatuni A.G. , Shahkhatuni A.G. , Petrosyan S.A. , Davinyan A.M. , Melikyan G.S. , Shahkhatuni A.A. , Shahkhatuni A.A. , Ananikov V.P.
4‐Heteryl‐Vinyl‐Butenolides as Visible‐Light T‐Type Photoswitches Quantified by Light‐Emitting Diode Nuclear Magnetic Resonance Spectroscopy
ChemPhotoChem. 2026. V.10. N9. e70294 . DOI: 10.1002/cptc.70294 WOS Scopus OpenAlex
Даты:
Опубликована online: 25 сент. 2026 г.
Идентификаторы БД:
≡ Web of science: WOS:001885997900001
≡ Scopus: 2-s2.0-105051696786
≡ OpenAlex: W7214312900
Альметрики: