| Project/Area Number |
18K05087
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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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| Review Section |
Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
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| Research Institution | Kyushu University |
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Principal Investigator |
Tani Fumito 九州大学, 先導物質化学研究所, 准教授 (80281195)
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| Project Period (FY) |
2018-04-01 – 2021-03-31
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| Project Status |
Completed (Fiscal Year 2020)
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| Budget Amount *help |
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2020: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2019: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2018: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
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| Keywords | アズレン / ヘリセン / 不斉 / 酸化 / ラジカル / 電子スピン / チオフェン / パイ電子 / パイ電子系 / 光物性 / カチオンラジカル / 光学活性 / 酸化還元 / HOMO-LUMOギャップ / キノン / パイ共役系 / 光学特性 |
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| Outline of Final Research Achievements |
Chiral helicene compounds that have helical pi-conjugated frameworks comprised of ortho-fused aromatic rings have been intensively investigated. On the other hand, there have been very few studies accomplishing thorough characterization of helicene radicals, although they are of profound interest from the standpoint of fundamental sciences and technological fields. Helicene radicals are unique chemical species in that they have a combination of chirality and unpaired electron spin(s) delocalized on helical pi-conjugated orbital(s). In order to obtain a stable helicene radical, a new helicene compound named AIBTh was synthesized. Electron-donating isobenzothiophene and 1,1’-biazulene units are fused to afford the helical structure of AIBTh, which is the first azulene-based chiral helicene. Upon one-electron oxidation of AIBTh, its air-stable cation radical was successfully isolated. The X-ray crystal structure and specific electronic structure of this cation radical were clarified.
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| Academic Significance and Societal Importance of the Research Achievements |
単一の分子内にキラリティと電子スピンの両方を有するヘリセンのラジカル種は基礎科学および工学的応用の両面から重要でありながら，不安定であるために，その実例は極めて限られていた。本研究では，この課題の解決に取り組み，アズレン骨格を採用した新しい化合物を合成し，安定なラジカル種を得ることにも成功した。ヘリセン化合物の安定ラジカル種を得るための有用な知見を明らかにした点に学術的な意義がある。
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