Facile fabrication of redox-active and electrochromic poly(amide-amine) films through electrochemical oxidative coupling of arylamino groups

Abstract

Two novel electropolymerizable monomers, namely 3,5-bis(4-diphenylaminobenzamido)-N-[4-(carbazol-9-yl)phenyl]benzamide (5) and 3,5-bis(4-diphenylaminobenzamido)-N-[4-(3,6-dimethoxycarbazol-9-yl)phenyl]benzamide (5-MeO), were synthesized, and their electrochemical properties were studied by cyclic voltammetry. The electron-withdrawing amide groups efficiently blocked the radical cations delocalization between the two terminal TPA groups, rendering the electropolymerization of the TPA groups feasible. The polymer electrodeposited from monomer 5 could be further crosslinked through electro-coupling of the carbazole groups, which showed both electrochromic and fluorescent properties (the emission of blue light (460 nm) in solid state). Both of the electro-generated polymer films derived from 5 and 5-MeO showed reversible electrochemical oxidation processes in the range of 0 − 1.4 V with strong color changes and high contrast ratios in the visible and NIR regions upon electro-oxidation. © 2016 The Authors. Journal of Polymer Science Part A: Polymer Chemistry Published by Wiley Periodicals, Inc. 2016, 54, 2476–2485.