Synthesis and solubility properties of amine-functionalized fulleropyrrolidines in organic solvents

In this study, we prepared amine-functionalized fullerene derivatives by using methylene blue (MB)-sensitized photoaddition reactions of fullerene C-60 with a variety of a-silyl group containing N-alkylglycinates through 1,3-dipolar cycloaddition reactions of in situ formed azomethine ylide, derived from glycinates, to fullerene C-60 and examined their solubility properties in several organic solvents. The results showed that although it was hard to find a clear correlation between the solvent solubility of and N-substituents of fullereopyrrolidines, the solubility of functionalized fullerene derivatives in organic solvents such as toluene, CHCl3, CH2Cl2, and tetrahydrofuran (THF) was much higher than that of C-60 and in addition, the solubility properties of fullereopyrrolidines can be manipulated by incorporating diverse organic moieties into fullerene surface.