Novel poly(arylene ethynylene) derivatives containing main chain triphenylamine and pendent quinoxaline moieties: synthesis and elementary characterization

Abstract

AbstractBACKGROUND: Various poly(arylene ethynylene)s (PAEs) have been prepared and applied as molecular wires, in sensors, in nonlinear optics and as electroluminescent materials. But, to our knowledge, there has been no attention paid to the investigation of conjugated PAEs containing both triarylamine and quinoxaline groups. The influence imparted by the introduction of triarylamine and quinoxaline on the photophysical and electrochemical properties of PAEs is of interest.RESULTS: Two kinds of novel PAE derivatives, with electron‐donating triphenylamine groups in the backbone and electron‐accepting pendent quinoxaline moieties and bearing side chains of different lengths, were successfully synthesized with the Sonogashira coupling reaction. These polymers are soluble in common organic solvents and exhibit good film‐forming ability and thermal stability. UV‐visible investigations indicate that the ground states of these materials are unaffected by the polarity of their medium. An efficient intramolecular charge transfer effect is observed from an investigation of their photoluminescence properties in different solvents. Cyclic voltammetry study reveals that these polymers possess relatively high highest occupied molecular orbital levels due to the incorporation of triphenylamine segments into the polymer backbones.CONCLUSION: Primary characterization of these novel PAE derivatives shows that they might serve as potential active materials in optoelectronic devices. Copyright © 2009 Society of Chemical Industry