Synthesis of triarylamine-containing poly(arylene ether)s by nucleophilic aromatic substitution reaction

Abstract

We report synthesis of a series of new triarylamine-containing AB-type monomers and their polymers via nucleophilic aromatic substitution (SNAr) reaction. Monomers consisting of a hydroxyl group at the para position of the nitrogen group in one phenyl ring and a fluorine leaving group at the para position in another phenyl ring were synthesized via palladium-catalyzed amination reaction. The fluorine leaving group was activated by trifluoromethyl group at the ortho position and an electron-withdrawing group (EWG) introduced at the para position of the unsubstituted phenyl ring that enabled control over monomer reactivity. SNAr reaction of the monomers successfully produced corresponding poly(arylene ether)s with pendant EWGs that exhibited good solubility and thermal stability. Optical and electrochemical properties of the polymers were also affected by incorporation of EWGs. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 2692-2702