Preparation and photochromic properties of 2,3-bisarylbenz[f]indenones

Abstract

From 2,3-dibromobenz[f]indenone, four compound: 2,3-bis(5-methyl-2-phenyl-4-thiazolyl)benz [f]indenone 10, 2,3-bis(3,5-dimethyl-4-isoxazolyl)benz[f]indenone 20, 3-(3,5-dimethyl-4-isoxazolyl)-2-(5-methyl-2-phenyl-4-thiazolyl)benz[f]indenone 30 and 2,3-bis(5-methyl-2-phenyl-4-thiazolyl)benz[f]indenol 40 were prepared, and their photochromic properties were investigated. Among them, photochrome 10 (weak photochromic) and its bisthiazolylbenz[f]indenol derivative 40 displayed photochromism. During ring closure photoreaction, photochrome 40 showed high conversion ratio (98.4%) with low diastereomeric excess (38%). (C) 2013 Elsevier B.V. All rights reserved.