The odd-numbered carbon clusters C119, C129, and C139 have been observ
ed in the mass spectra of toluene extracts of fullerene soots and of t
he products of ozone-fullerene reactions. Specifically, ozone-C60 reac
tions yield C119, ozone-C70 reactions yield C139, and ozone-(C60/C70)
reactions produce C119, C129, and C139. These unexpected species corre
spond to dimers of C60, C60/C70, and C70, respectively, less one carbo
n atom, and are stable gas-phase ions with behavior similar to that of
fullerenes. The results suggest a new route to functionalization and
derivatization of fullerenes through controlled ozone-catalyzed cage-o
pening reactions.