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Bandgap Engineering through Controlled Oxidation of Polythiophenes
Author(s) -
Wei Sujun,
Xia Jianlong,
Dell Emma J.,
Jiang Yivan,
Song Rui,
Lee Hyunbok,
Rodenbough Philip,
Briseno Alejandro L.,
Campos Luis M.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201309398
Subject(s) - polymer , monomer , homo/lumo , conjugated system , reagent , band gap , thiophene , materials science , polymer chemistry , photochemistry , chemistry , chemical engineering , organic chemistry , molecule , optoelectronics , engineering
The use of Rozen’s reagent (HOF⋅CH 3 CN) to convert polythiophenes to polymers containing thiophene‐1,1‐dioxide (TDO) is described. The oxidation of polythiophenes can be controlled with this potent, yet orthogonal reagent under mild conditions. The oxidation of poly(3‐alkylthiophenes) proceeds at room temperature in a matter of minutes, introducing up to 60 % TDO moieties in the polymer backbone. The resulting polymers have a markedly low‐lying lowest unoccupied molecular orbital (LUMO), consequently exhibiting a small bandgap. This approach demonstrates that modulating the backbone electronic structure of well‐defined polymers, rather than varying the monomers, is an efficient means of tuning the electronic properties of conjugated polymers.