Novel [60]fullerene polymers: Part 1: Synthesis and polymerisation processes through acrylation of N-methyl-o-hydroxy-2-phenyl fulleropyrrolidines and their monomers

Abstract

This synthesis of functionalized C60 and novel fullerene polymers is described by an extended acrylation functionality via pyrrolidine substitution. The strategy employed required that first C60 was derivatised to mono-fulleropyrrolidine (6,6 ring junctions of C60) was prepared and reacted with acryloyl chloride to obtain the monomer. Addition of azomethine ylide was found to provide a versatile method for derivatization of [60]fullerene. The first step in this study was to prepare low molecular weight hydroxy fulleropyrrolidines by [3 + 2] cycloaddition of azomethine ylide to [60]fullerene through the use of N-methyl glycine in conjunction with benzaldehyde derivatives. The fulleropyrrolidine monomer was made by the reaction of an –OH group of fulleropyrrolidine with acryloyl chloride in the presence of sodium hydroxide in absolute ethanol. The monomers were characterized by UV and FT-IR techniques. Polymerisation was carried out using benzoyl peroxide as a free radical initiator and dimethylformamide was used as a solvent. DMF is an eminently suitable solvent for compounds with a high molecular weight owing to the combined action of its small molecular size. During the polymerisation process it was observed that the monomer and polymer were soluble in DMF. In addition, the higher the dilution of the reactants, the lower the polymerisation rate and the lower the molecular weight of the product.