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Organic functionalization of graphene is successfully performed via1,3-dipolar cycloaddition of azomethine ylide in the liquid phase. Thecomparison between 1-methyl-2-pyrrolidinone and N,N-dimethylformamide asdispersant solvents, and between sonication and homogenization as dispersiontechniques, proves N,N-dimethylformamide and homogenization as the mosteffective choice. The functionalization of graphene nanosheets and reducedgraphene oxide is confirmed using different techniques. Among them,energy-dispersive X-ray spectroscopy allows to map the pyrrolidine ring of theazomethine ylide on the surface of functionalized graphene, while micro-Ramanspectroscopy detects new features arising from the functionalization, which aredescribed in agreement with the power spectrum obtained from ab initiomolecular dynamics simulation. Moreover, X-ray photoemission spectroscopy offunctionalized graphene allows the quantitative elemental analysis and theestimation of the surface coverage, showing a higher degree offunctionalization for reduced graphene oxide. This more reactive behaviororiginates from the localization of partial charges on its surface due to thepresence of oxygen defects, as shown by the simulation of the electrostaticfeatures. Functionalization of graphene using 1,3-dipolar cycloaddition isshown to be a significant step towards the controlled synthesis ofgraphene-based complex structures and devices at the nanoscale.

Covalent Organic Functionalization of Graphene Nanosheets and Reduced Graphene Oxide via 1,3-Dipolar Cycloaddition of Azomethine Ylide