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Issue 45, 2013
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Effect of different substituents on the water-solubility and stability properties of 1 : 2 [60]fullerene derivative·gamma-cyclodextrin complexes

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Abstract

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·γ-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.

Graphical abstract: Effect of different substituents on the water-solubility and stability properties of 1 : 2 [60]fullerene derivative·gamma-cyclodextrin complexes

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Publication details

The article was received on 23 Jul 2013, accepted on 30 Aug 2013 and first published on 03 Sep 2013


Article type: Paper
DOI: 10.1039/C3OB41513A
Citation: Org. Biomol. Chem., 2013,11, 7843-7851
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    Effect of different substituents on the water-solubility and stability properties of 1 : 2 [60]fullerene derivative·gamma-cyclodextrin complexes

    A. Ikeda, A. Hirata, M. Ishikawa, J. Kikuchi, S. Mieda and W. Shinoda, Org. Biomol. Chem., 2013, 11, 7843
    DOI: 10.1039/C3OB41513A

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