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Electropolymerizable Terthiophene S,S ‐Dioxide‐Fullerene Diels‐Alder Adduct for Donor/Acceptor Double‐Cable Polymers
Author(s) -
Vida Yolanda,
Suau Rafael,
Casado Juan,
Berlin Anna,
Navarrete Juan T. López,
PérezInestrosa Ezequiel
Publication year - 2007
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.200700174
Subject(s) - adduct , fullerene , acceptor , polymer , materials science , derivative (finance) , diels–alder reaction , macromolecule , photochemistry , polymer chemistry , chemistry , organic chemistry , catalysis , biochemistry , physics , financial economics , economics , condensed matter physics
The preparation of a novel fullerene‐thiophene derivative by Diels‐Alder addition of terthiophene S,S ‐dioxide was demonstrated. Extrusion of SO 2 from the adduct is an effective process that yields a stable cyclohexadiene‐1,4‐bisthiophene–C 60 adduct in good isolable yield. The product has been accurately characterized and opens the way to synthesize new C 60 derivatives “via” Diels‐Alder methodology without the possibility of cycloreversion. Electrochemical and spectroscopic properties of this macromolecule were studied and supported by theoretical calculations to interpret its electronic structure. The first approach to the electropolymerization of this macromonomer produces donor‐acceptor molecular wires providing a new and versatile way to fullerene‐based double cable polymers.