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.

Synthesis by oxidative polymerization of optically active, regioregular polythiophene from quinquethiophene monomer bearing chiral and n-dodecyl groups as substituents

ANGIOLINI, LUIGI;BRAZZI, ALICE;GRENCI, VALERIA;SALATELLI, ELISABETTA
2006

Abstract

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.
L. Angiolini; A. Brazzi; V. Grenci; E. Salatelli
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/32252
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