Exohedral Addition Chemistry of the Fullerenide Anions C and C .

A systematic screening study of the exohedral reactivity of the reduced fullerenes (fullerenides) C and C is reported. These doubly and singly negatively charged carbon cages were prepared by two-fold reduction of C with potassium, leading to K C , or by in situ monoreduction with the radical anion of benzonitrile PhCN , respectively. Several series of electrophiles, including geminal and distant dihalides, benzyl bromides, and diazonium compounds, were employed as addition partners.

Highly Regioselective Alkylation of Hexabenzocoronenes: Fundamental Insights into the Covalent Chemistry of Graphene.

Hexa-peri-hexabenzocoronides (HBC) was successfully used as a model system for investigating the complex mechanism of the reductive functionalization of graphene. The well-defined molecular HBC system enabled deeper insights into the mechanism of the alkylation of reductively activated nanographenes. The separation and complete characterization of alkylation products clearly demonstrate that nanographene functionalization proceeds with exceptionally high regio- and stereoselectivities on the HBC scaffold.

Synthesis, Structural Characterization, and Crystal Packing of the Elusive Pentachlorinated Azafullerene C NCl.

We report on the synthesis and the structure elucidation of the elusive azafullerene pentachloride C NCl , which was obtained by high temperature halogenation of (C N) . The exceptionally strong host-guest interaction of the title compound in the solid is discussed.

Solvent-driven electron trapping and mass transport in reduced graphites to access perfect graphene.

Herein, we report on a significant discovery, namely, the quantitative discharging of reduced graphite forms, such as graphite intercalation compounds, graphenide dispersions and graphenides deposited on surfaces with the simple solvent benzonitrile. Because of its comparatively low reduction potential, benzonitrile is reduced during this process to the radical anion, which exhibits a red colour and serves as a reporter molecule for the quantitative determination of negative charges on the carbon sheets. Moreover, this discovery reveals a very fundamental physical-chemical phenomenon, namely a quantitative solvent reduction induced and electrostatically driven mass transport of K(+) ions from the graphite intercalation compounds into the liquid.