Synthesis of High Aspect Ratio Bisphenols and Polycarbonates Incorporating Bisaryl Units

Abstract

Theoretical arguments linking monomer geometries to polymer fracture strengths and melt flow properties provide the rationale for design of a series of isomeric, high-aspect ratio bisphenols and new polycarbonates. An efficient synthesis of these monomers in addition to an optimal triphosgenation-based method for the synthesis of high molecular weight polycarbonates is presented. Preparation and polymerization of o-, meta-, and p-tetraaryl bisphenol A are reported, in addition to glass transition temperatures of the new polycarbonates. In accordance with expectations, the p- and m- isomers form ductile, amorphous high-heat films, while the o-isomer produces a relatively low-Tg brittle glass.