Design of a Series of Polythiophenes Containing C60 Groups: Synthesis and Optical and Electrochemical Properties

• Published in: Macromolecules Vol. 48; no. 2; pp. 323 - 336
• Main Authors: Perrin, Lara, Legros, Mathilde, Mercier, Régis
• Format: Journal Article
• Language: English
• Published: American Chemical Society 27.01.2015
• ISSN: 0024-9297; 1520-5835
• DOI: 10.1021/ma501788d

In order to develop polymers combining both acceptor and donor moieties, a series of alternating copolymers based on C60 fullerene and oligothiophenes were synthesized. First, a diamino-functionalized fullerene was obtained by a three-step modification of 4,4′-diaminobenzophenone, followed by a Bamford–Stevens addition on C60. A series of oligo-3-alkylthiophenes O3AT, with various polymer and alkyl chains lengths, were synthesized using the Grignard metathesis method and dicarbonylated by Vilsmeier formylation. Alternating copolymers [C60-O3AT] n were finally obtained by polycondensation, taking a specific care concerning synthesis conditions in order to optimize polymerization degrees. Nuclear magnetic resonance, infrared spectroscopy, gel permeation chromatography and thermogravimetric analysis were achieved in order to determine the structure of each copolymers. In addition, their functional properties (UV–vis absorption, photoluminescence, and electronic levels) were measured and related to the ascertained average compositions.