Synthesis and characterization of nitrated [60]fullerene derivatives

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.