Both p and n-Dopable, Multichromic, Napthalineimide Clicked Poly(2,5-dithienylpyrrole) Derivatives

Herein we disclose construction and characterization of both p- and n-dopable, multichromic 2,5-dithienylpyrrole (SNS) based electrochromic films and demonstrate usefulness of click chemistry on functionalization of SNS derivatives to enhance optoelectronic properties of the resultant polymer. For this purpose, 1,8-naphthalimide containing monomer (SNS-Napth) was synthesized through click chemistry for the first time. SNS-Napth was subjected to electrochemical polymerization and electrochromic properties of the resultant polymer was investigated in detail. Additionally, 16 different copolymers were synthesized by controlling electrochemical copolymerization conditions such as feed ratio, electrochemical polymerization method and potential. All the polymers revealed ambipolar redox behavior where reversible n- and p-type doping was achieved in cathodic and anodic regime, respectively. The homopolymer had a bandgap of 3.15 eV and displayed yellow-blue color variation upon doping. Copolymers, on the other hand, displayed multichromic behavior where a direct correlation between polymerization conditions (feed ratio, polymerization potential) and spectral behavior, color was determined. Among all copolymers, the ones which were synthesized in excess EDOT medium displayed higher reversibility and shorter switching times whereas amplification of polymerization potential seems to be ineffective in terms of switching times. (C) 2013 The Electrochemical Society. All rights reserved.