Energy profile of formal 1,2-dyotropic rearrangement of diarylethenes
https://doi.org/10.21285/2227-2925-2022-12-1-153-159
Abstract
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).
About the Authors
E. K. Kouame
Irkutsk National Research Technical University; A. E. Favorsky Irkutsk Institute of Chemistry SB RAS
Russian Federation
Russian Federation
Eric Koffi Kouame, Postgraduate Student
1, Favorsky St., Irkutsk, 664033; 83, Lermontov St., Irkutsk, 664074
A. G. Lvov
Irkutsk National Research Technical University; A. E. Favorsky Irkutsk Institute of Chemistry SB RAS
Russian Federation
Russian Federation
Andrey G. Lvov, Cand. Sci. (Chemistry), Leading Researcher
1, Favorsky St., Irkutsk, 664033; 83, Lermontov St., Irkutsk, 664074
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Review
For citations:
Kouame E.K., Lvov A.G. Energy profile of formal 1,2-dyotropic rearrangement of diarylethenes. Proceedings of Universities. Applied Chemistry and Biotechnology. 2022;12(1):153-159. https://doi.org/10.21285/2227-2925-2022-12-1-153-159
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