Claisen Rearrangement of Graphite Oxide: A Route to Covalently Functionalized Graphenes

Author(s)
Collins, William R.; Lewandowski, Wiktor; Schmois, Ezequiel; Walish, Joseph John; Swager, Timothy M
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Abstract
On the GO: The basal plane allylic alcohol functionality of graphite oxide (GO) can be converted into N,N-dimethylamide groups through an Eschenmoser–Claisen sigmatropic rearrangement by using N,N-dimethylacetamide dimethyl acetal. Subsequent saponification of these groups affords the carboxylic acids (see picture), which, when deprotonated, electrostatically stabilize the graphene sheets in an aqueous environment.
Date issued
2011-08
URI
http://hdl.handle.net/1721.1/74222
Department
Massachusetts Institute of Technology. Institute for Soldier Nanotechnologies; Massachusetts Institute of Technology. Department of Chemical Engineering; Massachusetts Institute of Technology. Department of Chemistry
Journal
Angewandte Chemie International Edition
Publisher
Wiley Blackwell
Citation
Collins, William R. et al. “Claisen Rearrangement of Graphite Oxide: A Route to Covalently Functionalized Graphenes.” Angewandte Chemie International Edition 50.38 (2011): 8848–8852.
Version: Author's final manuscript
ISSN
1433-7851
1521-3773
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