High Regioselective Cycloaddtion of Sc3N@C78 with Aryl Oxiranes

Abstract

Endohedral metallofullerenes (EMFs) with entrapping atoms and clusters have many superior properties due to the electron transfer from inner clusters to outer carbon cages, enabling them numerous potential applications in the fields of single molecule magnet, energy conversion, nano devices. The chemical functionalization of endohedral metallofullerenes through attraching different functional groups onto fullerene cage is useful strategy to improve corresponding solubility and tune the electron structure of endohedral metallofullerenes. Due to lower cage symmetry of Sc3N@D3h -C78 relative to that of Sc3N@Ih -C80, the high regioseletive synthesis of Sc3N@D3h -C78 derivatives have been a challenge in the fields of fullerene chemistry, howeer, is highly desired. Herein, we performed a photoreaction of Sc3N@Ih -C78 with asymmetric aryl oxirane in the toluene solution, leading to only main product among the possible 34 isomers. The X-ray single crystal diffraction measurement shows the [6,6]-close addition pattern of Sc3N@Ih -C78 derivative.