2001 Fiscal Year Final Research Report Summary
High-Performance Separation Systems Based on Kinetic Molecular Recognition
| Project/Area Number |
10208103
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| Research Category |
Grant-in-Aid for Scientific Research on Priority Areas (B)
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| Allocation Type | Single-year Grants |
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| Research Institution | Nagoya University |
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Principal Investigator |
OKAMOTO Yoshio Grad. School of Eng., Nagoya Univ., Professor, 工学研究科, 教授 (60029501)
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| Co-Investigator(Kenkyū-buntansha) |
HARADA Nobuyuki Tohoku Univ., Professor, 反応化学研究所, 教授 (30006324)
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| Project Period (FY) |
1998 – 2000
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| Keywords | Polysaccharide / Chiral Discrimination / HPLC / Chiral Stationary Phase / TLC / Immobilization / CD Exciton Chirality Method / Molecular Motor |
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| Research Abstract |
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.
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