1986 Fiscal Year Final Research Report Summary
Design and Development of Molecular Assembly Which Reveals High Function by An Electronic Interaction
| Project/Area Number |
60303005
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| Research Category |
Grant-in-Aid for Co-operative Research (A)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機化学一般
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| Research Institution | Faculty of Engineering, Ehime University
Kwansei Gakuin University |
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Principal Investigator |
TODA Fumio Ehime University, 工学部, 教授 (50036232)
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| Co-Investigator(Kenkyū-buntansha) |
MISUMI Soichi Osaka University, 産業科学研究所, 教授 (40029830)
OKAMOTO Kunio Kyoto University, 工学部, 教授 (90025841)
NAGAKURA Saburo Institute of Molecular Science, 教授 (30013444)
OKI Michinori Tokyo University, 理学部, 教授 (40011407)
ITO Sho Tohoku University, 理学部, 教授 (00004242)
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| Project Period (FY) |
1986 – 1987
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| Keywords | Molecular Assembly / Host-Guest Complex / Mutual Interaction / Design of Molecules Molecular Assembly / CT-Complex / Cyclophane Compound / Reaction Control / 光学活性化合物 |
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| Research Abstract |
Most of the molecular assembly by a weak interaction was designed using host-guest complexation method. Host compounds which were designed included a wide variety of organic compounds. Structure and molecular interaction, and molecular recognition ability of these host-guest complexes were studied. X-Ray analytical data of the complex were used for design of new host molecules.
Molecular recognition in the complex was used for isolation and optical resolution of compound. Since a host compound includes one compound selectively, the inclusion phenomena can be used for an isolation of isomer from a mixture. Since optically active host compound includes one enantiomer selectively, the phenomena can be used for an optical resolution. In these cases, host compound is recovered for to use again.
In the complex of achiral guest and chiral host, mutual chiral recognition between tham is present. Reaction of the guest compound in a solid state gave optically active compound. For example, irradiat
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ion of a 1:1 complex of (-)-1,6-di(o-chlorophenyl)-1,6-diphenylhexa-2,4-diyne-1,6-diol with tropolone alkyl ether in a solid state gave 100% optically pure [2+2] photocyclization product of the latter. The similar irradiation of a 1:1 complex of the same host compound as above and osoamide derivative gave 92% optically pure -lactam derivative.
Molecular assembly by a strong interaction was also studied on the following examples, cyclophanes, crown ethers, CT-complexes, complexes including metal compounds or metal ions. Structures, interactions, and chemical behaviors of these complexes were studied. Relation between intramolecular interaction and strain in a strained cyclophane was clarified. Behavior of a radical species in crown ether, and interaction of two triplet radical species through a crown ether ring were also studied. Intramolecular and intermolecular CT-interactions were studied for to develop high electronic conductors. Rhodium ion complex with a chiral organic molecule was develop for an enantioselective reaction. Less
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