Synthesis of functionalized fullerene-C₆₀ by the living anionic polymerization technique

The synthesis of functionalized fullerene-C₆₀ (C₆₀) was performed using living anionic polymerization. The metalation of the benzylic hydrogen atom on toluene or p-substituted toluene was conducted with the alkyllithium/amine system, and examined by living anionic polymerization of 1,3-cyclohexadiene. The number of carbanions bonded onto C₆₀ was estimated by the grafting reaction of living polymer onto C₆₀. The tert-butyllithium/N,N,N′,N′-tetramethylethylenediamine system was an effective metalation reagent, and toluene-, p-xylene-, 4-methyltriphenylamine-functionalized C₆₀s having good solubility were successfully synthesized.