Chemistry of Strained Conjugation System:Synthesis and Properties of Highly Strained Carbon sigma-Bond and 4 pi Antiaromatic Molecules
| Project/Area Number |
15K05412
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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 | Hiroshima University (2017)
University of Tsukuba (2015-2016) |
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Principal Investigator |
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| Project Period (FY) |
2015-04-01 – 2018-03-31
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| Project Status |
Completed (Fiscal Year 2017)
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| Budget Amount *help |
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
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| Keywords | シクロブタジエン / 反芳香族性 / 高歪結合 / ビラジカル / 光異性化 / シグマ共役 / 高歪み結合 / 反芳香族分子 / 原子価異性化 / 開殻一重項 / テトラヘドラン |
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| Outline of Final Research Achievements |
Tetrahedrane is a hydrocarbon with highly strained C-C sigma bonds and one of the valence isomers of cyclobutadiene. Therefore, thermally stable tetrahedrane derivatives are considered as the best synthetic precursors of elusive cyclobutadiene derivatives. Recently we have developed a quantitative and reliable method for synthesizing cyclobutadiene by photo-induced isomerization of the corresponding tetrahedrane precursors. Since cyclobutadiene is a molecule with highly strained 4 pi antiaromatic molecules, research of a stable compound was limited. In this study, we successfully synthesized a sterically and electronically stabilized antiaromatic molecule using silicon substituents. Up to now, more than 20 stable tetrahedrane derivatives have been successfully synthesized, and most of them could be converted into corresponding isomer of cyclobutadienes. We also succeeded in the first observation of triplet cyclobutadiene by variable temperature EPR measurement.
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Report
(4 results)
Research Products
(28 results)
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[Journal Article] Isolation of Hypervalent Group-16 Radicals and Their Application in Organic-Radical Batteries.2016
Author(s)
Yasuyuki Imada, Hideyuki Nakano, Ko Furukawa, Ryohei Kishi, Masayoshi Nakano, Hitoshi Maruyama, Masaaki Nakamoto, Akira Sekiguchi, Masahiro Ogawa, Toshiaki Ohta, and Yohsuke Yamamoto
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Journal Title
Journal of American Chemical Society
Volume: 138
Issue: 2
Pages: 479-482
DOI
Related Report
Peer Reviewed
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