Synthesis and characterization of nitrated [60]fullerene derivatives

摘要

A synthetic method for the preparation of monodisperse hexanitro[60]fullerenes 1_6 was developed. The use of 1_6 as a reactive precursor in the synthesis of organo-amino derivatives of C_(60) 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 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 mlz 901 was correlated to the composition of its parent compound 1_6, as hexanitro[60]fullerenes containing 6 nitro addends per C_(60) cage.