Effect of different substituents on the water-solubility and stability properties of 1 : 2 [60]fullerene derivativeEgamma-cyclodextrin complexes

Atsushi Ikeda, Akiko Hirata, Michiko Ishikawa, Jun-ichi Kikuchi, Shunsuke Mieda, and Wataru Shinoda

Org. Biomol. Chem. 11, 7843-51 (2013).

We have demonstrated that C60 derivatives bearing a pyrrolidine moiety as well as a variety of other substituents can form 1:2 complexes with γ-cyclodextrin (γ-CDx) using a mechanochemical high-speed vibration milling apparatus. When the influence of the steric hindrance of the substituents on the formation of the complexes was negligible, the water-solubilities of the complexes were shown experimentally to be completely dependent on the hydrophobic properties of the substituent. Furthermore, the stabilities of the γ-CDx-complexes of several different C60 derivatives were found to be similar to or slightly higher than that of the C60Eγ-CDx complex, with the solubilities of the complexes showing no correlation to the stabilities. Based on the results of a series of theoretical investigations, we have shown that the stabilities of the γ-CDx-complexes can be affected not only by steric effects but also by the polarities of the substituent groups, which exist in the vicinity of the upper rim of γ-CDx, because the water bound to the polar group can assist in the stabilisation of the complexes.