2018 Fiscal Year Final Research Report
Construction of a catenan library using fluorous tags to explore the functional search of catenane molecules
| Project/Area Number |
16K05690
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Niigata University |
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Principal Investigator |
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| Project Period (FY) |
2016-04-01 – 2019-03-31
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| Keywords | カテナン / ライブラリー / フルオラスタグ / オレフィンメタセシス |
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| Outline of Final Research Achievements |
Synthesis of catenanes was carried out by olefin metathesis, oxidative homo-coupling reaction of terminal alkynes, and Husigen reaction between alkyne with azide. Reaction conditions to introduce fluorous tags into nitrogen atoms of catenanes was investigated. Thus, trifluoromethanesulfonyl- and pentafluorobenzenesulfonyl-groups were introduced to catenanes to obtain the corresponding fluorous-tagged catenanes in good yields. Due to the steric hindrance of sulfonyl groups, rotation of the rings of the catenanes was blocked to give topological isomers.
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| Free Research Field |
構造有機化学・超分子化学
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| Academic Significance and Societal Importance of the Research Achievements |
３個以上の環状分子が連結した高次カテナンは、複数の外部刺激に応じて多段階で応答する高次複合刺激応答分子システムや、複数の相互作用部位を集約的に配置した特異的分子認識システムの構築が期待できる。本研究では、高次カテナンの合成法を確立し、高次カテナンの分離精製の足がかりとなるフルオラスタグの導入に成功した。これらの成果は今後、カテナンライブラリーの構築、そして、カテナンの新規機能性材料、ナノ分子デバイス、ナノ分子スイッチへの応用展開が期待できる。
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