Claisen Rearrangement of Graphite Oxide: A Route to Covalently Functionalized Graphenes
Author(s)Collins, William R.; Lewandowski, Wiktor; Schmois, Ezequiel; Walish, Joseph; Swager, Timothy Manning
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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.
DepartmentMassachusetts Institute of Technology. Institute for Soldier Nanotechnologies; Massachusetts Institute of Technology. Department of Chemical Engineering; Massachusetts Institute of Technology. Department of Chemistry
Angewandte Chemie International Edition
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.
Author's final manuscript