Semiconducting polymers from triphenylamine derivatives-benzaldehyde polymers by oxidization with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)

摘要

4-Tolyldiphenylamine (TDPA) and N,N'-diphenyl-N,N'-bis(4-methylplienyl)-1,1'-biphenyl-4,4'-diamine (TPD), were reacted with benzaldehyde (BA) using p-toluenesulfanic acid as a catalyst to yield linear polymers. The polymers were reacted with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in tetrahydrofuran (THF) at room temperature. 1{sup left}H-NMR showed that all the methine protons in the residue of BA were completely removed at the male ratio of repeating unit:DDQ, 2:1. The resulting polymers showed good solubility in chloroform or THF. The reacted TDPA-BA and TPD-BA polymers gave new UV absorption peaks at 697.0 and 722.5 nm and showed reversible redox potentials about 0.994 and 1.021 V, respectively. Direct current (d.c.) conductivity of the reacted polymers was in the range of 10{sup}(-11)S/cm, which is more than two orders higher than the unreacted polymers. The polymer showed pen tad split electron spin resonance (ESR) signal, whose concentration was one in 670 or 230 repeating unit for TDPA-BA and TPD-BA polymers, respectively.