Author:

Keywords:

chiral, conjugated polymers, polythiophenes, supramolecular structures, synthesis, stable oxidized state, polymers, chirality, poly(3-alkoxythiophene)s, polymerization, solvent, fecl3, Science & Technology, Physical Sciences, Polymer Science, CHIRALITY, POLY(3-ALKOXYTHIOPHENE)S, POLYMERIZATION, POLYMERS, 0303 Macromolecular and Materials Chemistry, 0306 Physical Chemistry (incl. Structural), 0912 Materials Engineering, Polymers, 3403 Macromolecular and materials chemistry, 3406 Physical chemistry

Abstract:

The synthesis, aggregation, and optical properties of a chiral, regioregular polythiophene, substituted with a conjugated substituent, are described. The polymer was prepared using a Stille coupling reaction. The fact that the side-chain contributes to the absorption (UV-vis), emission (fluorescence), and redox behavior (cyclic voltammetry) of the material demonstrates that the substituent contributes to the electronic properties. It was shown that the conjugated side-chain chirally stacks in conditions in which the polymer backbone aggregates, which demonstrates the ability of conjugated polymers to induce a (chiral) lamellar organization of conjugated moieties, present in their side-chain. The aggregation of both the side-chain and the backbone was monitored using UV-vis and CD spectroscopy. Finally, it is shown that the conjugated side-chain can selectively be oxidized, without oxidizing the polythiophene backbone. (C) 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 1891-1900, 2009