Synthesis, characterization, thermal, electrical and electrochemical studies of oligo nitrobenzimidazoles and their p–n diode applications

Abstract

Three novel nitro oligobenzimidazoles, oligo-2-(6-nitro-1H-benzo[d]imidazol-2-yl)phenol (OBINP2), oligo-3-(6-nitro-1H-benzo[d]imidazol-2-yl)phenol (OBINP3) and oligo-4-(6-nitro-1H-benzo[d]imidazol-2-yl)phenol (OBINP4) were synthesized by oxidative polycondensation of benzimidazole monomers with NaOCl in aqueous alkaline medium. The structure of the monomers and oligomers were confirmed by FT-IR, UV–Vis, 1H and 13C NMR spectroscopic techniques. The monomer BINP2 and its oligomer are showing dual emission through excited state intramolecular proton transfer process. The band gap values of monomers and oligomers were calculated from both UV–Vis spectroscopic and cyclic voltammetric data. Theoretical band gap values of monomers obtained from DFT were compared with experimentally calculated band gap values. The electrical conductivity of I2 doped and undoped oligomers were measured using two point probe technique and are showing good correlation with the charge densities on imidazole nitrogen obtained from Huckel method. The conductivity of oligomers increases with increase in iodine vapour contact time up to 144 h. The variation of dielectric properties of oligomers has been investigated at different frequency and temperature. Among the oligomers, OBINP3 is having greater thermal stability as evidenced by its high carbine residue of around 65% at 600 °C in thermogravimetric analysis.