Synthesis and Characterization of a Fully Aromatic Polyazomethine with Main Chain Rotaxane Architecture

Abstract

A new aromatic polyazomethine with rotaxane architecture containing a blocking group in every structural unit has been synthesized by polycondensation of 3,6-diformyl-9-butyl carbazole with p,p′-diaminobiphenyl (benzidine)/β-cyclodextrin adduct. As compared with polymers obtained in the absence of β-cyclodextrin, this polymer is more hygroscopic and soluble in polar solvents such as DMF and DMSO. The IR, 1H-NMR, GPC and DSC data support the presence of β-cyclodextrin in the polymer chain. Measurements made by gel permeation chromatography of the DMF soluble main-chain polyrotaxane show high molecular weight. This polymer is a light-yellow coloured product and its electrical conductivity is as high as 10−9 S cm−1. Doping with iodine markedly increased the conductivity of the orange-brown coloured semiconductive polyazomethine with a maximum conductivity of 10−6 S cm−1.