High-Performance Separation Systems Based on Kinetic Molecular Recognition

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1. Cyclohexylcarbamates of cellulose and amylose were prepared and their resolving abilities for enantiomers were evaluated as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC). The CSPs showed high resolving abilities, and could also be used for thin-layer chromatography (TLC). These derivatives were soluble in chloroform and exhibited chiral discrimination to some chiral compounds in 1H NMR spectroscopy as well as in HPLC.2. Chitin is a readily available polysaccharide with 1,4-glycosidic linkage as well as cellulose and amylose. However, until recently this polysaccharide had not successfully been used for the preparation of CSPs for HPLC. We have found a suitable method for the preparation of chitin carbamates, such as 3,5-dimethyl, 4-chloro and 4-trifluoromethylphenylcarbamates, with relatively high chiral recognition abilities. The CSPs of chitin 3,5-dimethyl and 3,5-dichlorophenylcarbamates can be used in the presence of chloroform as a component of eluents owing to their poor solubilities in the eluent.3. A new cellulose phenylcarbamate derivative having a vinyl group was synthesized and immobilized onto silica gel via radical copolymerization with styrene. The resulting CSPs could be stably used under chromatographic conditions with a chloroform as an eluent.4. A new strategy for determining the absolute configuration of mono-functional compounds by the CD exciton chirality method was proposed. Some achiral CD auxiliaries with two naphthalene chromophores were designed, and the absolute configurations of chiral mono-alcohols and chiral mono-amines could be determined by this new strategy.5. The first light-powered chiral molecular motor, which photochemically rotates only in one-direction reflecting the chirality of the motor molecule was successfully constructed. The motor rotation was composed of a chiral and helical olefin, and its rotation was controlled by the irradiation of light and molecular chirality.