Investigations on the electrochemical properties of new conjugated polymers containing benzo[c]cinnoline and oxadiazole moieties

A four-step route was designed to synthesize 3,8-benzo[c]cinnoline dicarboxylic acid (4). New conjugated polymers, POXD (I) and POXD (T), containing benzo[c]cinnoline and oxadiazole moieties, were obtained by thermal cyclodehydration of their soluble polyhydrazide precursors PHA (I) and PHA (T), respectively. Two reduction peaks were observed for these new conjugated polymers during CV cathodic scan. From the CV voltammograms combined with the results from molecular simulation, we concluded that the first reduction occurred at oxadiazole moiety and benzo[c]cinnoline moiety was responsible for the second reduction. It indicates that oxadiazole has stronger electron affinity than benzo[c]cinnoline. We proposed a mechanism to explain this two-stage reduction process. Due to the planar and electron-accepting ability of benzo[c]cinnoline and oxadiazole moieties, POXD (I) and POXD (T) exhibited very low LUMO (−3.42 and −3.45 eV) and HOMO (−6.23 and −6.27 eV) energy levels. They can be used as hole-blocking or electron-injection layers for OLED applications.