大環状ホスト化合物を用いる糖の分子認識
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概要
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Resorcinol cyclic tetramer (calix [4] resorcinarene) binds hydroxylic guest compounds including sugars in apolar organic media. The driving force of this complexation is a combination of hydrogen bonding and CH-πinteraction. The latter interaction gives rise to not only a 1 : 1 host : guest stoichiometry but also a sizable selectivity arizing from the apolar alkyl moiety of the guests. Sugars and related guests can also be bound in water to tetrasulfonate derivatives of the host. The CH-π interaction again provides the major driving force. It is sensitive to the π-electron density of the aromatic cavity of the host. Thus, the guest (sugar) binding ability of the host is enhanced either by introduction of additional electron-donating OH groups on the benzene rings or upon deprotonation of the OH groups giving rise to anionic host. The CH-π interaction may be regarded as a kind of hydrogen bonding between π-base and σ-acid.