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

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

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 aci...

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Veröffentlicht in:Angewandte Chemie International Edition 2011-09, Vol.50 (38), p.8848-8852
Hauptverfasser: Collins, William R., Lewandowski, Wiktor, Schmois, Ezequiel, Walish, Joseph, Swager, Timothy M.
Format: Artikel
Sprache:eng
Schlagworte:
Claisen rearrangement
electrostatic stabilization
graphene
surface functionalization
water solubility
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Zusammenfassung: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201101371