Facile synthesis of isomerically pure fullerenols C60(OH)5Br and 1,4-C60(OH)2 from chlorofullerene C60Cl6

Abstract

The chlorofullerene C60Cl6 was demonstrated as a versatile precursor for the synthesis of two isomerically pure fullerenols via tetrabutylammonium bromide promoted reactions with water. Performing the synthesis in wet chlorobenzene produced 1,4-C60(OH)2 as the only isolable product along with substantial amounts of non-functionalized C60. However, the addition of DMSO as a co-solvent altered the reaction pathway, leading to the formation of C60(OH)5Br as the main product. Both isolated compounds were novel and their molecular compositions and structures were confirmed by mass spectrometry and NMR spectroscopy. The fullerenol C60(OH)5Br, which was formed in a moderate yield, represents the first isomerically pure polyhydroxylated fullerene available on a large scale.