2020 Fiscal Year Final Research Report
Synthesis and application of novel polycyclic conjugated systems involving azaphenalenyl moieties
| Project/Area Number |
18K05091
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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 | University of Hyogo |
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Principal Investigator |
Kawase Takeshi 兵庫県立大学, 工学研究科, 教授 (10201443)
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| Project Period (FY) |
2018-04-01 – 2021-03-31
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| Keywords | 含窒素芳香族化合物 / アザフェナレニル / アゾメチンイリド / カチオンラジカル / 含窒素ナノグラフェン |
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| Outline of Final Research Achievements |
N-Substituted 2-azaphenalenyl is of particular interest because of its unique electronic structure; however, it has been known as a reactive intermediate owing to its azomethine ylide character. We first synthesize N-phenyl and N-2,6-di(isopropyl)phenyl-2-azaphenalenyl derivatives 1 and 2 by basic treatments of the corresponding iminium salts. N-phenyl derivative 1 dimerizes at 1,3 positions during the isolation process, indicating that the p-system has a biradical character. On the other hand, 2 can be isolated as a deep green crystal. An X-ray crystal analysis and spectral analysis reveal the structural and electronic properties. Especially, electrochemical experiments (CV) also reveal a considerably high electron donating property of 2. Moreover, chemical oxidation with silver ion of 2 afforded the corresponding radical cation 3 as a dark amber crystals. An X-ray analysis, ESR spectral analysis and theoretical calculation have explored the structural and electronic properties.
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| Free Research Field |
構造有機化学
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| Academic Significance and Societal Importance of the Research Achievements |
窒素原子を含む縮合多環状共役系化合物（含窒素ナノグラフェン）は，炭素原子のみで形成された縮合多環状共役系化合物と比べて，特異な光・電子特性を示すことが知られている。本研究ではアザフェナレニル構造をもつ共役系化合物を合成することを目的として、嵩高い置換基を持つ2-アザフェナレニル誘導体とそのカチオンラジカルを合成した。Ｘ線結晶構造解析や各種スペクトルによって構造や電子状態の解明を行なった。これらの研究をさらに発展させることで、多様な含窒素共役系化合物の構築が可能になると思われる。それらの化合物は高い酸化還元能が期待され，有機半導体，光材料，さらには燃料電池触媒への応用に発展するものと期待される。
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