Simultaneous Reduction and Functionalization of Graphene Oxide via Ritter Reaction

Graphene oxide, the oxidized form of graphite, is a common precursor to conductive nanosheets and used widely in the preparation of composite materials. GO has the benefits of easy exfoliation and handling, but it tends to aggregate and restack when reduced. One approach to overcoming this undesired aggregation is covalent modification of the nanosheets; however, this typically requires additional reagents and time. Herein, we report the simultaneous reduction and functionalization of graphene oxide using the Ritter reaction such that reduced nanosheets show good conductivity without the aggregation typical of unmodified material. GO reacts with nitriles in strongly acidic conditions to give highly reduced graphene oxide (C:O of 4.38:1) with covalently attached amides, which compatibilizes it to a number of organic solvents. This Ritter-type reaction produces carbocations on the basal plane of graphene oxide, which allows nucleophilic attack by the nitrogen of the nitrile and produces amides upon hydrolysis. The product has sheet resistance (57.60 ± 4.04 kω/sq) substantially lower than that of the starting graphene oxide (529.60 ± 10.04 kω/sq) and, more importantly, can easily be dispersed in various organic solvents and does not restack into graphite-like materials upon drying. This method yields individual conductive nanosheets that can be readily incorporated into a number of different systems.