Synthesis and characterization of some novel polythiophene derivatives containing pyrazoline

Abstract

Eight polythiophene derivatives containing pyrazoline side groups were synthesized by a chemical oxidative coupling polymerization using FeCl3. The crystal structures of four monomers were determined which confirm the almost perpendicular orientation of the thiophene and pyrazoline rings, while the other substituents are more coplanar. Analyses of IR, 1H-NMR, Raman and UV-Vis spectra demonstrated that the suggested polymerization was successful to generate the synthesized polythiophenes with the expected structures. The morphology of the synthesized polythiophenes was studied by SEM. The different substituents attached to the 1- and 3-positions of the pyrazoline side chain led to differences in optical properties, electrical conductivity, and thermal stability of the synthesized polythiophenes. By adding a pyrazoline side chain to polythiophenes, some polymers achieve good solubility, electrical conductivity of about 1.3 × 10–6 S/cm, high fluorescence intensity (above 40,000 a.u.) at 505–550 nm and thermal stability up to 590°C in the air.

Keywords

• polythiophene derivatives
• pyrazoline heterocycle
• chemical polymerization
• crystal structure