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Mechanism of Photochromic Transformations and Photodegradation of an Asymmetrical 2,3-Diarylcyclopentenone

Abstract

The mechanistic study of photochromism and photodegradation of an asymmetrical thiophene-containg 2,3–diarylcyclopent-2-en-1-one bearing a thiophene and a benzothiophene rings (3-(2,5-dimethiltiofen-3-il)-2-(2-methil-1-benzyltiofen-3-il)cyclopent-2-en-1-on, compound 1) has been performed using stationary photolysis, nanosecond laser flash photolysis and time-resolved luminescence. Photochromic properties of 1 are typical for diarylethenes involving light-induced transitions between open form 1A and closed form 1B. Photodegradation occurs via two mechanisms. The first oxygen-free mechanism is the formal 1,2-dyotropic rearrangement. The second oxygen-dependent mechanism includes excitation of 1A to the triplet state, its quenching by dissolved oxygen and oxidation of the initial compound by singlet oxygen.

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Article information


Submitted
22 Oct 2019
Accepted
06 Feb 2020
First published
06 Feb 2020

Phys. Chem. Chem. Phys., 2020, Accepted Manuscript
Article type
Paper

Mechanism of Photochromic Transformations and Photodegradation of an Asymmetrical 2,3-Diarylcyclopentenone

M. V. Oplachko, A. Smolentsev, I. M. Magin, I. P. Pozdnyakov, V. A. Nichiporenko, V. P. Grivin, V. F. Plyusnin, V. V. Vyazovkin, V. V. Yanshole, M. V. Parkhats, A. V. Yadykov, V. Z. Shirinian and E. Glebov, Phys. Chem. Chem. Phys., 2020, Accepted Manuscript , DOI: 10.1039/C9CP05744G

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