The synthesis and characterization of an optically active quinquethiophene monomer 3,3””-didodecyl-4’,3”’-di[(S)-(+)-2-methylbutyl]- 2,2’:5’,2”:5”,2”’:5”’,2””-quinquethiophene [(S)-(+)-DDDMBQT], bearing at the C-β positions of thiophene rings both linear C12 alkyl chain and chiral, enantiomerically pure, alkyl group is described. The polymerization of [(S)-(+)-DDDMBQT] by oxidative mechanism has been optimized in terms of yield of soluble polymer with high molecular weight.The obtained polymeric derivative displays enhanced conjugation extension with respect to similar poly(3-alkylthiophene)s reported in the literature and optical activity in the spectral region related to the chromophore absorptions when in the microaggregate state, indicative of the presence of supramolecular chiral conformations.
Abstract:The spectroscopic behavior of thin films of regioregular poly(alkylthiophene)s bearing an optically active alkyl group has been investigated in the solid state under different sample preparation procedures. The experimental results are interpreted in terms of influence of the side-chain substituents on the extent of planarity of the polymeric chains and the formation of optically active chiral aggregates.
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