Synthesis of water-soluble polyhydroxylated C/sub 60/ derivatives and their uses in polymer network

Summary form only given. Fullerene molecules exhibit a high reactivity towards both nucleophilic substitutions and electronic reductions. Unlike most of highly conjugated aromatics, they are relatively inert to the electronic oxidation showing a remarkable stability even under doping with arsenic pentafluoride at solid state. We demonstrated that the reactivity of electrophilic substitution on fullerenes can be significantly enhanced. We outline methods for the preparation of polyhydroxylated fullerene derivatives through the reaction of fullerenes with electrophilic reagents. The synthetic methods include the aqueous acid chemistry and the nitronium chemistry for the conversion of fullerenes to fullerols. Structure of this type of fullerols was characterized to consist of hemi-ketal functions linked with an enol ether in addition to tertiary hydroxy groups. Novel synthesis of fullerols involves the hydrolysis of polysulfated fullerene precursors, which were prepared from the reaction of C/sub 60/ with H/sub 2/SO/sub 4-/SO/sub 3/ under N/sub 2/ at 55-60/spl deg/C. These new fullerols with a simple chemical composition of C/sub 60/ carbons and hydroxy groups, exhibits significant improvement on the stability in acidic media and on the solubility in various organic solvents. Design and reaction conditions of fullerol with various reactive bifunctional monomers resulted in high performance polymeric derivatives with enhanced physical properties will be discussed.