2004 Fiscal Year Final Research Report Summary
Studies on Synthesis and Properties of Cyclophanes Based on the Bridged[14]π-Annulene Units
| Project/Area Number |
14540499
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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 |
Organic chemistry
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| Research Institution | Saga University |
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Principal Investigator |
YAMATO Takehiko Saga University, Faculty of Science and Engineering, Applied Chemistry, Professor, 理工学部, 教授 (60136562)
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| Project Period (FY) |
2002 – 2004
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| Keywords | Bridged aromatic compounds / Cyclophanes / Dihydropyrene / Transannular interaction / CH-π interaction / Charge-transfer interaction / Photocromism / Molecular device |
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| Research Abstract |
1.The development of synthesis of the bridged aromatic copounds
Although there are numerious reports concerning synthesis of the bridged aromatic compounds, their preparative routes seem to be too lomg for practical purposes. Especially, the [2.2]metacyclophane-dienes and their valence tautomers trans-10b,10c-dihydropyrenes are so highly strained compounds that may be reactive towards many reagents. However, the chemistry of these cornpouns is very limited. In this work, we have developed the convenient preparation of the strained bridged aromatic compounds having the double bouns on bridged chaines using the tertbutyl function as a positional protecting group on the aromatic ring. Based on these synthetic results, we have succeeded to prepare the cyclophanes constructed by the bridged [14]π-annulene units.
2.Relationship between the structures and chemical reactivity
Electrophilic substitution reactions of metacyclophane-dienes and dihydropyrenes were studied in order to investigate the relationship between the reactivity and the molecular strains. We have observed a various kinds of transannular reaction and isomerizarion due to the release of the molecular strains.
3.Relationship between the structures and photochemical properties
We have investigated the photochemical properties of cyclophane-dienes and 10b,10c-dimethyl-10b,10c-dihydropyrenes. The relationship between the structures and physical properties was also investigated by X-ray diffraction analysis.
4.The development to the advanced materials
Based on the photochemical properties of cyclopanes, we have investigated the photo-induced valence tautomerization of 10b,10c-dimethyl-10b,10c-dihydropyrenes to 8,16-dimethyl[2.2]metacyclophane-1,9-dienes. We have succeeded to construct the new photocromic systems and devdoped to the application for the advanced materials, for example photo-response molecular recognition systems.
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Research Products
(51 results)
