Thermally reversible photochromism of dipyrrolylethenes

Photochem Photobiol Sci. 2019 Sep 11;18(9):2136-2141. doi: 10.1039/c8pp00557e.

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.