Open AccessFacile fabrication of redox‐active and electrochromic poly(amide‐amine) films through electrochemical oxidative coupling of arylamino groups
Author(s) -
Hsiao ShengHuei,
Wang HuiMin
Publication year - 2016
Publication title -
journal of polymer science part a: polymer chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.768
H-Index - 152
eISSN - 1099-0518
pISSN - 0887-624X
DOI - 10.1002/pola.28124
Subject(s) - electrochromism , monomer , carbazole , polymer chemistry , electrochemistry , amide , cyclic voltammetry , polymer , photochemistry , chemistry , redox , oxidative coupling of methane , materials science , organic chemistry , electrode , methane
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