Single-walled carbon nanotubes (SWCNTs) and C60 are functionalized by reactions with di-Me acetylenedicarboxylate (DMAD) and alcs. mediated by 4-(dimethylamino)pyridine (DMAP) to give adducts such as the oxocyclopentenofullerene I. The reactions are proposed to occur by addn. of zwitterions generated from DMAP and DMAD to C60 or SWCNTs with concomitant ring closure followed by substitution of the (dimethylamino)pyridinium moiety of the intermediate adducts with alcs. Reaction of SWCNTs with DMAP, DMAD, and 1-dodecanol yields functionalized carbon nanotubes with significantly greater solubilities in org. solvents than unfunctionalized SWCNTs. The structure of I•CS2 is detd. by X-ray crystallog. [on SciFinder(R)]
