vuzbiochemiИзвестия вузов. Прикладная химия и биотехнологияProceedings of Universities. Applied Chemistry and Biotechnology2227-29252500-1558ИРНИТУ10.21285/2227-2925-2022-12-1-153-159vuzbiochemi-761Research ArticleКРАТКИЕ СООБЩЕНИЯBRIEF COMMUNICATIONЭнергетический профиль формальной 1,2-диотропной перегруппировки диарилэтеновEnergy profile of formal 1,2-dyotropic rearrangement of diaryletheneshttps://orcid.org/0000-0002-6351-3335КуамеК. Э.KouameE. K.

К. Э. Куаме, аспирант

664033, г. Иркутск, ул. Фаворского, 1; 664074, г. Иркутск, ул. Лермонтова, 83,

Eric Koffi Kouame, Postgraduate Student1, Favorsky St., Irkutsk, 664033; 83, Lermontov St., Irkutsk, 664074

erickofikouame@gmail.comhttps://orcid.org/0000-0003-2951-2651ЛьвовА. Г.LvovA. G.

А. Г. Львов, к.х.н., ведущий научный сотрудник; заведующий лабораторией664033, г. Иркутск, ул. Фаворского, 1; 664074, г. Иркутск, ул. Лермонтова, 83

Andrey G. Lvov, Cand. Sci. (Chemistry), Leading Researcher1, Favorsky St., Irkutsk, 664033; 83, Lermontov St., Irkutsk, 664074

lvov-andre@yandex.ruИркутский национальный исследовательский технический университет; Иркутский институт химии им. А. Е. Фаворского СО РАНРоссияIrkutsk National Research Technical University; A. E. Favorsky Irkutsk Institute of Chemistry SB RASRussian Federation202201042022121153159Copyright © Куаме К.Э., Львов А.Г., 20222022Куаме К.Э., Львов А.Г.Kouame E.K., Lvov A.G.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://vuzbiochemi.elpub.ru/jour/article/view/761

Диарилэтены с тиофеновыми заместителями относятся к фотопереключаемым соединениям (фотопереключателям или фотохромам). При облучении УФ-светом их исходная форма (ДАЭ-o) превращается в фотоиндуцированный изомер (ДАЭ-c), при этом обратная реакция индуцируется облучением видимым светом. Множественное фотопереключение обычно приводит к необратимой фотоперегруппировке ДАЭ-c в аннелированные изомеры ДАЭ-а, которые устойчивы фотохимически и термически. В данной работе нами были оптимизированы структуры ряда диарилэтенов, а также их изомеров на уровне теории B3LYP/6-31G(d). Впервые обнаружено, что ДАЭ-а дестабилизированы относительно ДАЭ-с на 1,71–14,00 ккал/моль. Эти результаты важны для разработки молекул и материалов, которые способны необратимо менять свои свойства под действием света.

Diarylethenes with thiophene substituents belong to photoswitchable compounds (photoswitches or photochromes). Upon UV irradiation, their colorless open-ring isomers (DAE-o) convert to the colored closed-ring isomers (DAE-c), while the back reaction is induced only by visible light irradiation. A multiple photoswitching of diarylethenes usually results in irreversible photorearrangement of DAE-c to the so-called annulated isomers DAE-a, that are stable thermally and photochemically. In the present communication, structures of a series of diarylethenes as well as their isomers were optimized on the B3LYP/6-31G(d) level of theory. It was disclosed for the first time, that DAE-a destabilized relatively DAE-c by 1.71–14.00 kcal/mol. These results are important for design of photocontrollable molecules and materials, operated in the oneway (permanent manner).

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The authors declare that there are no conflicts of interest present.