Development of Materials for Asymmetric Recognition by Chiral Modification of Ordered Mesoporous Materials

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Mesoporous silica AMS (anionic surfactant templated mesoporous silica) with helical particles were successfully synthesized by using the chiral anionic surfactants N-miristoyl derivatives of D- and L-alanines (C_<14>-L-AlaA and C_<14>-D-AlaA), as well as D- and L-valines (C_<14>-L-ValA and C_<14>-D-ValA). The left-/right-handed ratios for the helical particles synthesized with L-isomers and D-isomers proved to be 75/25 and 25/75, respectively, suggesting that the predominant handedness of helices was directed by the handedness of the surfactants. The synthesis conditions for obtaining a chiral mesoporous silica have been optimized. The macroscopic morphology as well as the mesostructure of the chiral mesoporous silica was extremely sensitive to the synthetic conditions. The influence of the stereoisomerism of the chiral surfactant on the mesostructure and morphology of chiral AMS was investigated by using a mixture of C_<14>-L-AlaA and C_<14>-D-AlaA. Helical rod-shaped AMS was found to be effective for asymmetric separation of recemic trifluoroacetylalanine ethyl ester (CF_3CO-Ala-Oet). Synthesis of AMS by using asparagin derivatives has also been investigated.