Development of chiral nano-space using highly-ordered molecular gel for molecular recognition

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Glutamide-derivatives with a triethoxysilyl group (CmGDD) was newly synthesized and confirmed to form fibrous self-assembly in various organic solvents. CmGDD was grafted onto the surface of porous silica particles through siloxane bonds (Sil-CmGDD) for use in reversed-phase HPLC as a stationary phase. Solid-state 13C NMR and DSC measurements indicate that CmGDD can form highly-oriented structures on the silica surface. The Sil-C10GDD packed-column was investigated by retention studies of polycyclic aromatic hydrocarbons. The chromatographic results showed that the Sil-CmGDD provided excellent selectivity for these isomers such as stilbenes and terphenyls than conventional octadecylated silica. It is estimated that these preferable results can be brought about through hydrogen bond-mediated molecular orientation of weak interaction sites such as carbonyl groups. Sil-CmGDD also showed excellent separations of bio-related molecules such as tocopherols isomers and Vitamine Ds.