Synthesis and Polymerization of Methacrylate Having Fullerene

Abstract

Two methacrylate monomers containing fullerene on the side chain (AHMA-C60 or AEMA-C60) were synthesized by reacting 4-azidobenzoyloxy-hexyl and -ethyl methacrylate, respectively, with fullerene. 1H and 13C NMR spectra of these monomers revealed each was a mixture of [6,6] bridged azamethanofullerene derivative and azafulleroid derivative resulting from [5,6] additions. The monomers were later copolymerized with t-butyl methacrylate. In the case of anionic copolymerization using a Grignard reagent, the monomers were incorporated in the polymer chain via vinyl chain reactions, resulting in a charm bracelet type fullerene polymer. The copolymer composition was found almost equal to the composition of monomers fed. In radical copolymerizations, low molecular weight oligomers were obtained in low yields, and contained almost equal amounts of the vinyl group to the fullerene monomer incorporated in the polymer, indicating that the fullerene unit played a role of an inhibitor or a degradative chain transfer agent.