Poly(triphenylamine)s derived from oxidative coupling reaction: Substituent effects on the polymerization, electrochemical, and electro‐optical properties

Abstract

Abstract A series of triphenylamine‐based polymers containing electron‐donating methoxy (OCH 3 ) and electron‐withdrawing cyano or nitro (CN or NO 2 ) substituents in the main chains have been designed and investigated. These conjugated polymers ( P1 – P3 ) could be readily prepared by oxidative coupling polymerization from monomers ( M1 – M3 ) using FeCl 3 as an oxidant. The P2 and P3 exhibited moderate high T g values (203–205 °C) and thermal stability. These polymers in NMP solution showed UV–vis absorption around 288–404 nm and photoluminescence peaks around 435–492 nm. P1 – P3 showed reversible oxidation redox couples at E onset = 0.67, 0.99, and 1.00 V in solution of 0.1 M tetrabutylammonium perchlorate (TBAP)/acetonitrile (CH 3 CN), respectively. M3 and P3 exhibited reversible reduction redox couples at E onset = −1.04 and −1.03 V. These polymers also revealed electrochromic characteristic changing color at different potential. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 285–294, 2009