Synthesis and characterization of nitrated [60]fullerene derivatives

A synthetic method for the preparation of monodisperse hexanitro[60]fullere nes 1(6), was developed; The use of 1(6), as a reactive precursor in the sy nthesis of organo-amino derivatives of C-60 was also demonstrated. The ally lic tert-nitro moieties in hexanitro[60]fullerenes were found to be excelle nt leaving groups for nucleophilic substitutions by amino nucleophiles, suc h as anilines, leading to the formation of hexaanilino[60]fullerenes. Negat ive ion desorption chemical ionization mass spectra (DCI--MS) of both hexaa nilino[60]fullerene and hexanitroso[60]fullerene, a hydride-reduced product of 1(6),were utilized for substantiation of the number of nitro groups per C-60 in 1(6). Detection of the molecular ion of C-60(NO)(6) at m/z 901 was correlated to the composition of its parent compound 1(6), as hexanitro[60 ]fullerenes containing 6 nitro addends per C-60 cage.