Synthesis, characterization and properties of azobenzene side‐chain polythiophene

Thiophene monomers with an azobenzene moiety of different spacer length at the 3-position of the thiophene ring were synthesized. The monomers were polymerized and copolymerized with 3-hexyl thiophene to investigate the influence of an azobenzene side-chain on the properties of polythiophene, which has been widely used as a conducting polymer and has also been found many other applications. The polymers were characterized with UV-vis, FT-IR spectrophotometry, gel permeation chromatographic (GPC) analysis, DSC, TGA, elemental analysis and X-ray diffractometry. The polymers showed novel thermochromic and photoresponsive properties in polymer solutions and solid films. It was found that an azobenzene side-chain could bring about substantial thermochromic and photochromic changes to the polythiophene backbone as compared with non-azobenzene side-chain polythiophenes. These property changes could be triggered or controlled by light or heat on the basis of azobenzene trans–cis or cis–trans isomerization. Copyright © 2003 John Wiley & Sons, Ltd.

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