Poly(amine‐amide‐imide)s Bearing Pendent <i>N</i>‐Carbazolylphenyl Moieties: Synthesis and Electrochromic Properties

Abstract

Abstract Summary: A series of novel poly(amine‐amide‐imide)s with pendent N ‐carbazolylphenyl units that have inherent viscosities of 0.45–0.66 dL · g −1 are prepared from various aromatic bis(trimellitimide)s and the new carbazole‐based aromatic diamine, 4,4′‐diamino‐4″‐ N ‐carbazolyltriphenylamine, by direct polycondensation. All the polymers are readily soluble in polar organic solvents. Flexible, amorphous, and deep reddish films of poly(amine‐amide‐imide)s can be obtained by solution casting, and have useful levels of thermal stability associated with high glass transition temperatures (307–343 °C), 10% weight‐loss temperatures in excess of 500 °C, and char yields at 800 °C in nitrogen higher than 65%. These polymers exhibit a maximum UV‐vis absorption at 300 nm with a fluorescence emission maxima around 449–454 nm in N ‐methyl‐2‐pyrrolidinone solution. The hole‐transporting and electrochromic properties are examined by electrochemical and spectroelectrochemical methods. Cyclic voltammograms of the poly(amine‐amide‐imide) films cast onto an indium tin oxide‐coated glass substrate exhibit a reversible oxidation at 0.84 V and irreversible oxidation redox couples at 1.27 V versus Ag/AgCl in acetonitrile solution, and reveal good stability of electrochromic characteristics, with a color change from yellowish to green at applied potentials ranging from 0.00 to 0.95 V. Structure and properties of PAI‐2M (bottom left: cyclic voltammetry; bottom right: potential‐step absorptometry). image Structure and properties of PAI‐2M (bottom left: cyclic voltammetry; bottom right: potential‐step absorptometry).