Effect of different substituents on the water-solubility and stability properties of 1:2 [60]fullerene derivative•gamma-cyclodextrin complexes
Effect of different substituents on the water-solubility and stability properties of 1:2 [60]fullerene derivative•gamma-cyclodextrin complexes
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不同取代基对1:2[60]富勒烯衍生物•γ-环糊精配合物水溶性及稳定性的影响
DOI：
10.1039/c3ob41513a
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发表时间：
2013
期刊：
影响因子：
--
通讯作者：
W. Shinoda
中科院分区：
文献类型：
--
作者：
A. Ikeda;A. Hirata;M. Ishikawa;J. Kikuchi;S. Mieda;W. Shinoda
我们利用机械力化学高速振动研磨装置证明了含有吡咯烷基团的C60衍生物以及其他各种取代基可以与环糊精形成1- ： -2络合物(γ-γ)。当取代基的空间位阻对络合物形成的影响可以忽略时，络合物的水溶性完全依赖于取代基的疏水性质。此外，几种不同C60衍生物的γ-CDX-络合物的稳定性与C60·γ-CDX络合物相似或略高于C60·CDX-络合物，而络合物的溶解度与稳定性无关。根据一系列理论研究的结果，我们发现γ-CD_x-络合物的稳定性不仅受空间位阻效应的影响，而且还受γ-CD_x上缘附近取代基极性的影响，因为与极性基团结合的水有助于络合物的稳定。
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.