The reaction of silica-supported 60fullerene with vaporous nonylamine at 150 deg C produces a mixture of addition products. Quantum chemical calculations, at the B3LYP/STO-3G level of theory, support that the addition reaction most likely takes place across the 6,6 bonds of C_(60) pyracyclene units (and not across the 5,6 bonds). Numerous peaks were found in high-performance liquid chromatograms, apparently due to a large number of possible isomers. According to elemental analysis data (C:N ratio), the number of nonylamine molecules attached to C_(60) is 3 on average. Thermogravimetric analysis of the nonylamine adduct showed two weight losses, one between 360 and 590 deg C due to thermal decomposition of nonylamine moieties, and one between 725 and 840 deg C due to decomposition of the remaining fullerene-derived carbonized material. Field-desorption mass spectrometric study revealed a number of molecular and fragment ions corresponding to the adducts with up to six nonylamine moieties attached to 60fullerene; some of them were observed as multiply-charged ions. The temperature behavior of these peaks is similar to that for TGA, with maxima shifted to lower temperatures due to the cooperative effect of the strong electric field. C_(60) can be partially regenerated by pyrolysis of the nonylamine adduct. although at very low yields (below 1 percent, after heating at 350 deg C under air for 2 h).
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