A facile one-pot synthesis of novel amphiphilic perfluoroalkyl ester functionalized γ-cyclodextrin and complex formation with anionic surfactants

γ-Cyclodextrin (γ-CyD) was hydrophobically modified by selective functionalization at the C-6 position (primary face) with fluoroalkyl ester groups. This new amphiphilic γ-CyD was prepared in a facile one-pot synthesis by direct esterification of γ-CyD with perfluorobutanoic acid on the narrow rim of macrocylic molecule. The selective per-substituted product, octakis (6-O-perfluorobutanoyl)-γ-cyclodextrin (γ-CyD-F), was confirmed by 1H NMR, 13C NMR and 19F NMR spectroscopic methods. The complexing ability of the γ-CyD-F was investigated with different types of anionic surfactant having single or double hydrophobic tail groups. Predominant complex formation was observed in all cases with an equimolar mixture of surfactant and γ-CyD-F in methanol irrespective of the type of the surfactant.

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