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Angew Chem Int Ed Engl. 2014 Feb 10;53(7):1832-6. doi: 10.1002/anie.201309398. Epub 2014 Jan 21.

Bandgap engineering through controlled oxidation of polythiophenes.

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1
Department of Chemistry, Columbia University, 3000 Broadway, MC3124, New York, NY 10027 (USA) http://camposgroup.chem.columbia.edu.

Abstract

The use of Rozen's reagent (HOF⋅CH3 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.

KEYWORDS:

Rozen’s reagent; donor-acceptor systems; n-type materials; polythiophene

PMID:
24505004
DOI:
10.1002/anie.201309398
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