Synthesis and characterization of poly(quinoxaline vinylene)s and poly(pyridopyrazine vinylene)s with phenyl substituted side-groups

Poly(quinoxaline vinylene) and poly(pyridopyrazine vinylene) with 3(2′-ethylhexyloxy)phenyl side-groups have been synthesized and compared with similar polymers with purely aliphatic side-chains. The new polymers had smaller bandgaps, and from cyclic voltammetry it was seen that the phenyl substituted side-groups made the polymers easier to reduce, with half wave potentials of −1.02 and −1.33 V versus Ag/AgCl for the poly(pyridopyrazine vinylene) and poly(quinoxaline vinylene) respectively. The attachment of the phenyl substituted side-groups had counteracting effects on the stability towards photo-oxidation, which resulted in improved stability of the poly(pyridopyrazine vinylene) compared to its equivalent with purely aliphatic side-chains, while the poly(quinoxaline vinylene) showed decreased stability.