Functionalization of fullerene soot through oxidative decarboxylative coupling with silver dinitrobenzoate

Abstract

In this research, we extend the functionalization of fullerene soot with nitroaryl substituents through oxidative decarboxylative coupling with silver 3,5-dinitrobenzoate. For this purpose, silver 3,5-dinitrobenzoate is first prepared in two-steps from 3,5-dinitrobenzoic acid. Then, this compound as a substrate together with potassium persulfate as an oxidant is used in acetonitrile as a solvent to functionalize fullerene soot. The reactions with different equivalent ratios of substrate and oxidant are conducted by both thermal and microwave conditions. This strategy is able to induce about 88.03 wt.% O and 5.79 wt.% N to the composition of fullerene soot. The advantage of this strategy is that the reaction can happen without the need for a catalyst, because silver(I) present in the substrate can catalyze the reaction progress. To prove the functionalization, several characterization techniques are used, i.e. XRD patterns, EDX spectra and SEM elemental distribution images, FE-SEM and TEM micrographs, particle size distribution histograms, FT-IR and Raman spectra, as well as TGA and DSC curves, which demonstrate the changes on fullerene soot. The novelty of this research is that it provides a new strategy for oxidative decarboxylative coupling of silver(I) carboxylates with the carbon surface.