Synthesis and characterization of nitrated [60]fullerene derivatives

Abstract

A synthetic method for the preparation of monodisperse hexanitro[60]fullerenes 1₆ was developed. The use of 1₆ as a reactive precursor in the synthesis of organo-amino derivatives of C₆₀ was also demonstrated. The allylic tert-nitro moieties in hexanitro[60]fullerenes were found to be excellent leaving groups for nucleophilic substitutions by amino nucleophiles, such as anilines, leading to the formation of hexaanilino[60]fullerenes. Negative ion desorption chemical ionization mass spectra (DCI^–-MS) of both hexaanilino[60]fullerene and hexanitroso[60]fullerene, a hydride-reduced product of 1₆, were utilized for substantiation of the number of nitro groups per C₆₀ in 1₆. Detection of the molecular ion of C₆₀(NO)₆ at m/z 901 was correlated to the composition of its parent compound 1₆, as hexanitro[60]fullerenes containing 6 nitro addends per C₆₀ cage.