Synthesis and characterization of fluorescent poly(oxadiazole)s containing 3,4-dialkoxythiophenes

Abstract

We report the synthesis, optical and electrochemical details, and properties of three conjugated copolymers (P1-P3) consisting of alternate hole-transporting thiophene derivative and electron-transporting 1,3,4-oxadiazole units. The polymers are prepared using the precursor polyhydrazide route. The polymers have well defined structure and exhibit good thermal stability with the onset decomposition temperature in nitrogen at around 300 C. All the polymers are soluble in organic solvents such as DMF, DMSO, NMP and in strong organic acids like trifluoroacetic acid. The optical and charge-transporting properties of the polymers are investigated by UV-visible spectroscopy, fluorescence emission spectroscopy and cyclic voltammetry. The UV-visible absorption spectra of polymers in solution showed a maximum at around 400 nm. The polymers depicted green fluorescence both in solution and as thin films. Cyclic voltammetry studies reveal that these copolymers have low-lying LUMO energy levels ranging from -3.28 to -3.36 eV and high-lying HOMO energy levels ranging from -5.5 to -5.56 eV, which indicated that they may be promising candidates for electron-transporting or hole-blocking materials in light-emitting diodes. 2006 Elsevier B.V. All rights reserved.