Efficient one-flask synthesis of water-soluble [60]fullerenols

Abstract

C60 molecule exhibited high reactivity towards the addition reaction of nitrogen dioxide radicals (·NO2), which were generated by reaction of sodium nitrite with conc. HNO3. This chemical functionalization of C60 resulted in polynitro fullerenes, C60(NO2)(n). Hydrolysis of polynitro fullerenes in aqueous NaOH gave the corresponding polyhydroxylated fullerene derivatives (fullerenols) in moderate overall yields. Results from mass spectra (FAB, negative ion) of fullerenols indicated their structure as C60 derivatives with at least 16 hydroxy groups.