Fullerene derivatization by pyrolytic reaction

The first observation of C{sub 60} was made in a time-of-flight mass spectrometer and mass spectrometry continues to play a major role in the identification of fullerenes and fullerene derivatives. Since the discovery of a method of producing macroscopic quantities of fullerenes, many fullerene derivatives have been reported and an increasing number have been fully characterized. The identification of the molecular weight of fullerene derivatives in reaction mixtures has been invaluable. Mass spectrometry has provided evidence for a plethora of novel compounds including metallic, alkyl, aryl, benzyl, phenyl, hydroxy, amino, fluoro, epoxy, and hydro fullerenes. In this study, new aromatic derivatives of C{sub 60} are produced by reaction with aryne or aryl radicals which are pyrolytically generated. The products are characterized by desorption chemical ionization mass spectrometry in the negative ion mode. Because of the high electron affinity of C{sub 60} abundant radical anions of C{sub 60} and derivatives are produced under chemical ionization conditions and can be detected in crude reaction mixtures with no sample preparation.