Substituent effects on the photochromic properties of benzothiophene-based derivatives

Chemistry. 2015 Jun 1;21(23):8471-82. doi: 10.1002/chem.201500647. Epub 2015 Apr 27.

Abstract

Five diarylethene photochromic derivatives, the structures of which incorporate a central benzothiophene unit, a left-hand thiazole group, and a right-hand benzothiophene group, have been prepared. The compound with a thiazole unit with no substituent on the reaction-center carbon atom reveals an unprecedented transformation upon light irradiation. When the 4-position of thiazole is protected by a methyl group, the compounds show high photosensitivity and photochromic properties. In this case, light irradiation affords new compounds with [5]helicene structures featuring the highest redshifted absorption maxima reported to date.

Keywords: arylation; helical structures; isomerization; photochromism; substituent effects.