Organic Photocatalyst for Polymerization Reactions: 9,10-Bis[(triisopropylsilyl)ethynyl]anthracene

A new organic photocatalyst (9,10-bis[(triisopropylsilyl)ethynyl]anthracene, An-Si) is proposed here for the formation of free radicals under very soft irradiation conditions under air through a photoredox catalysis. It works according to an oxidative cycle that uses the combination of An-Si, a diphenyl iodonium salt along with a silane. This behavior is highlighted through an investigation of its excited state and redox properties. The different chemical intermediates are characterized by ESR experiments. In addition, the reversibility of the oxidation reaction of An-Si was investigated by cyclic voltammetry. This three-component system is able to promote the ring-opening photopolymerization of an epoxide as well as the free radical photopolymerization of an acrylate upon household LED bulb and Xe lamp exposure. Excellent polymerization profiles (mainly in ROP) are obtained. The specific properties of this catalyst are outlined.