2020 Fiscal Year Final Research Report
Experimental Verification of Three-Dimensional Aromaticity
Project/Area Number |
20K20366
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Project/Area Number (Other) |
18H05353 (2018-2019)
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Research Category |
Grant-in-Aid for Challenging Research (Pioneering)
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Allocation Type | Multi-year Fund (2020) Single-year Grants (2018-2019) |
Review Section |
Medium-sized Section 33:Organic chemistry and related fields
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Research Institution | Osaka University |
Principal Investigator |
Tobe Yoshito 大阪大学, 産業科学研究所, 招へい教授 (60127264)
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Co-Investigator(Kenkyū-buntansha) |
家 裕隆 大阪大学, 産業科学研究所, 教授 (80362622)
久木 一朗 大阪大学, 基礎工学研究科, 教授 (90419466)
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Project Period (FY) |
2018-06-29 – 2021-03-31
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Keywords | 芳香族性 / 反芳香族性 / 三次元積層構造 / 電子状態 / 分子構造 |
Outline of Final Research Achievements |
The purpose of this study is to experimentally verify the three-dimensional aromaticity, which is a new theoretically proposed concept for antiaromatic compounds. For this purpose, a 28-pi electron antiaromatic tetracyclopentatetraphenylene bearing four [(triisopropyl)silyl]ethynyl groups was synthesized. As a result of crystal structure analysis, it was clarified that it had a structure in which the molecules adopted two- or three-layer geometry, depending on the crystal preparation conditions. In both cases, each molecule possessed highly symmetrical aromatic structures. Moreover, from the chemical shift of the solid-state proton NMR spectrum, it was clarified that this molecule exhibited aromatic properties, the magnitude of which was alternating depending on the layer numbers. In this way, the results not only verified the proposed theory but also further extended it.
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Free Research Field |
有機化学
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Academic Significance and Societal Importance of the Research Achievements |
芳香族化合物は一般に安定であるため、多くの最先端機能材料に用いられることで現代社会を支えているが、電子数の規則性が異なる反芳香族化合物は反応性が高いため全く利用されてない。本研究は、反芳香族化合物について理論的に提唱された新たな概念である三次元芳香族性を実験的に検証することを目的に行った。実際、検証に適した分子を合成しそれが結晶中で積層した配置をとる際に芳香族的な挙動を示すことを確かめた。この成果は、成熟した有機化学の分野に新風を吹き込み活性化させるという学術的な意義だけでなく、これまで注目されてこなかった反芳香族化合物の機能材料への利用の道も開くという社会的な意義を有する。
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