2018 Fiscal Year Final Research Report
Synthesis of face-to-face oligomers of antiaromatic compounds and elucidation of their aromaticity
| Project/Area Number |
17K14447
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Organic chemistry
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| Research Institution | Osaka University |
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Principal Investigator |
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| Project Period (FY) |
2017-04-01 – 2019-03-31
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| Keywords | 反芳香族性 / 芳香族性 / ポルフィリノイド / ポルフィリン |
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| Outline of Final Research Achievements |
In this study, I aimed the observation of the inversion of aromaticity through face-to-face stacking of antiaromatic compounds. I adapted isophorin derivatives, which are two-electron reduced species of porphyrins, as antiaromatic compounds suitable for stacking. We investigated the stabilization and aromaticity of unstable isophorin derivatives. Attempts to stack the obtained antiaromatic isophorins by the metallation have been failed. I also investigated the methods for the face-to-face staking of the stable aromatic analogues. As a result, synthesis of rare-earth porphyrin double- and triple-decker complexes and covalently-linked face-to-face dimers was achieved, and their structure and properties were also revealed. I also preliminary observed the unusual emission behavior of the obtained antiaromatic compounds.
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| Free Research Field |
有機化学
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| Academic Significance and Societal Importance of the Research Achievements |
本研究では、温和な条件化で可逆的に芳香族―反芳香族性をスイッチングすることが可能な分子を創製した。このスイッチングにより、顕著に吸収、発光、磁気特性が変化することを明らかにした。本成果は、周囲の環境変化に応答するセンサー材料などへの応用が期待される。
また、本研究は、分子が重なりあうことで発現する特異的な芳香族性、および付随する物性の発現を目的としており、一部それを示唆する結果が得らえた。得られた知見を元にその詳細を明らかにすることで、有機化学における非常に重要な概念である芳香族・反芳香族性の拡張につながることが期待される。
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