1996 Fiscal Year Final Research Report Summary
SYNTHESIS OF CALIXRESORCINARENES AS BUILDING BLOCKS FOR SUPRAMOLECULAR CHEMISTRY
| Project/Area Number |
07651060
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Synthetic chemistry
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| Research Institution | TOTTORI UNIVERSITY |
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Principal Investigator |
KONISHI Hisatoshi TOTTORI UNIVERSITY FACULTY OF ENGINEERING,PROFESSOR, 工学部, 教授 (40112106)
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| Project Period (FY) |
1995 – 1996
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| Keywords | supramolecule / macrocycle / calixarene / calixresorcinarene / cyclophane / molecular recognition / thiomethylation |
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| Research Abstract |
Chiral calixresorcinarenes were prepared via mono-O-benzyl derivatives. Thier molecular chirality were investigated by NMR spectroscopy. The NMR titration of the macrocycle with a chiral trimethylammonium compound showed the host-guest complexation with enantioselective molecular recognition ability.
Two bromine substituents were selectively introduced at the diametrical positions of calixresorcinarene. The regioselectivity of the bromination was discussed.
Introduction of thiomethyl groups between two hydroxyl groups on the resorcinol nuclei was conducted. By using this method, macrocycles having a deep hydrophobic cavity were synthesized.
The acid-catalyzed condensation of 2-alkylresorcinols with formaldehyde was investigated. The reaction gave cyclic tetramer, pentamer and hexamer as major products. The pentamer and hexamer readily isomerized to the tetramer under acidic conditions. The pentamer was isolated and characterized by spectroscopy.
The functionalized calixresorcinarenes prepared in this study are promising building blocks for the construction of novel molecules in the field of supramolecular chemistry.
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Research Products
(8 results)
