Functionalized Poly(3-hexylthiophene)s via Lithium–Bromine Exchange
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Swager_Functionalized Poly.pdf
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Author(s)
Koo, Byungjin
Sletten, Ellen M.
Swager, Timothy M
Date Issued
December 2014
Journal
Macromolecules
Publisher
American Chemical Society (ACS)
Citation
Koo, Byungjin; Sletten, Ellen M. and Swager, Timothy M. "Functionalized Poly(3-hexylthiophene)s via Lithium–Bromine Exchange." Macromolecules 48, 1 (December 2014): 229–235 © 2014 American Chemical Society
Version
Final published version
Abstract
Poly(3-hexylthiophene) (P3HT) is one of the most extensively investigated conjugated polymers and has been employed as the active material in many devices including field-effect transistors, organic photovoltaics and sensors. As a result, methods to further tune the properties of P3HT are desirable for specific applications. Herein, we report a facile postpolymerization modification strategy to functionalize the 4-position of commercially available P3HT in two simple steps–bromination of the 4-position of P3HT (Br–P3HT) followed by lithium−bromine exchange and quenching with an electrophile. We achieved near quantitative lithium–bromine exchange with Br–P3HT, which requires over 100 thienyl lithiates to be present on a single polymer chain. The lithiated-P3HT is readily combined with functional electrophiles, resulting in P3HT derivatives with ketones, secondary alcohols, trimethylsilyl (TMS) group, fluorine, or an azide at the 4-position. We demonstrated that the azide-modified P3HT could undergo Cu-catalyzed or Cu-free click chemistry, significantly expanding the complexity of the structures that can be appended to P3HT using this method.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Massachusetts Institute of Technology. Department of Materials Science and Engineering
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DOI of Published Version
https://doi.org/10.1021/ma5019044
