Issue 9, 2019

Thermally reversible photochromism of dipyrrolylethenes

Abstract

Although diarylethene derivatives are considered to undergo thermally irreversible photochromic reactions, this is not always the case. Here, we report on thermally reversible photochromic diarylethenes having pyrrole-2-carbonitrile aryl groups. The thermal stability of the coloured closed-ring isomer of 1,2-bis(2-alkyl-5-cyano-1-methyl-3-pyrrolyl)perfluorocyclopentene was found to depend on alkyl substituents at the 2- and 2′-positions. The closed-ring isomer of the ethyl-substituted derivative thermally returned back to the open-ring isomer much faster than that of the methyl-substituted derivative. The difference in the thermal stability was well explained by the ground state energy difference between open- and closed-ring isomers. Excellent fatigue resistance and appropriate thermal fading rates were observed for the derivative having cyano substituents at the 5- and 5′-positions and methyl substituents at the 2-, 2′-, 4- and 4′-positions. The UV-irradiated colouration and thermal decolouration cycle can be repeated more than 103 times.

Graphical abstract: Thermally reversible photochromism of dipyrrolylethenes

Supplementary files

Article information

Article type
Paper
Submitted
05 Des. 2018
Accepted
24 Jan. 2019
First published
27 Jan. 2019

Photochem. Photobiol. Sci., 2019,18, 2136-2141

Thermally reversible photochromism of dipyrrolylethenes

K. Inaba, R. Iwai, M. Morimoto and M. Irie, Photochem. Photobiol. Sci., 2019, 18, 2136 DOI: 10.1039/C8PP00557E

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