Photoswitch based on remarkably simple naphthopyrans

Abstract

Photochromic switches built around 5-carbonyl-3,3-diphenyl-3 H-naphtho[2,1- b]pyran unit have been synthesized. Their open forms are constituted of a 1:1 ratio of TC and TT-isomers according to 19F and 1H NMR investigations. Electrocyclization of TT isomers back to the closed form is efficiently achieved upon visible irradiation whereas it has been found to be a particularly unfavoured thermal process. These simple 2H-chromenes could act as molecular photoswitch at ambient temperature.