Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 7, Pages 1832-1836Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201309398
Keywords
donor-acceptor systems; n-type materials; polythiophene; Rozen's reagent
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Funding
- Center for Re-Defining Photovoltaic Efficiency through Molecule Scale Control, an Energy Frontier Research Center (EFRC)
- U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences [de-sc0001085, de-sc0001087]
- NYSTAR
- Office of Naval Research [N000141110636]
- Division Of Materials Research
- Direct For Mathematical & Physical Scien [1112455] Funding Source: National Science Foundation
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The use of Rozen's reagent (HOFCH3CN) 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.
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