Solution-processable and electroactive aromatic polyamides with 3,5-bis(trifluoromethyl)triphenylamine moiety

Newfluorine-containing, triphenylamine-baseddiamine anddicarboxylic acidmonomers, namely3,5-bis(trifluoromethyl)-4', 4''-diaminotriphenylamine and 3,5-bis(trifluoromethyl)-4', 4''-dicarboxytriphenylamine, were synthesized and polymerized with commercially available aromatic dicarboxylic acids and diamines, respectively, leading to two series of aromatic polyamides, 5a-h and 7a-e. Most of the polyamides were amorphous and readily soluble in many common organic solvents and could be solution-cast into transparent, flexible and strong films with good mechanical properties. The polyamides had useful levels of thermal stability associated with high glass transition temperatures of 273-305 degrees C and 10% weight-loss temperatures in excess of 500 degrees C. Cyclic voltammograms of films of polymers 5a-h on indium-tin oxide-coated glass substrates exhibited reversible oxidation redox couples with E-1/2 around 1.15 V versus Ag/AgCl in tetrabutylammonium perchlorate/acetonitrile solution, accompanied by a color change from colorless neutral state to reddish brown oxidized state. The 7 series polymers displayed a higher oxidation potential and less electrochemical stability as compared to the 5 series analogues. (C) 2017 Society of Chemical Industry