Development of facile synthesis of fluorescent heterohelicenes
| Project/Area Number |
16K05710
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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 | Anan National College of Technology |
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Principal Investigator |
OTANI Takashi 阿南工業高等専門学校, 創造技術工学科, 准教授 (70339109)
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| Project Period (FY) |
2016-04-01 – 2020-03-31
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| Project Status |
Completed (Fiscal Year 2019)
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| Budget Amount *help |
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2018: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2017: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2016: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
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| Keywords | ヘリセン / アザヘリセン / 円偏光発光 / 超原子価ヨウ素 / 脱水素環化 / 簡便合成法 / 光学活性 / 分子内カップリング / 含窒素複素環 / 有機化学 / 有機物理化学 |
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| Outline of Final Research Achievements |
Helicenes are a class of ortho-fused aromatic rings that have been pursued due to their stable chiral helical structures. By virtue of the curved pi-electron system, optically active helicenes exhibit circularly polarized luminescence (CPL) properties in addition to strong circular dichroism (CD) and extremely high optical rotation. Although general helicenes are less fluorescent (e.g. the quantum yield of parent [7]helicene is only 0.02), fluorescent helicenes have been developed by the substitution of benzene rings into heterocycles and/or nonhexagonal rings. We have developed a two- or three-step synthesis of polyaza[5]-[9]helicenes by consecutive N-H coupling with a hypervalent iodine reagent. We further evaluated their photophysical properties, and circularly polarized luminescence properties and found that glum values increase with the number of fused rings up to 2.7 x 10-2, which is the highest value among [9]helicenes.
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| Academic Significance and Societal Importance of the Research Achievements |
ヘリセンは芳香環がオルト位で縮環したらせん状の非平面多環式芳香族化合物であり，末端同士の立体反発によるキラリティーを有することから，新しい有機材料としての応用が期待されている．しかし，ヘリセンの合成には一般に多段階を要し，蛍光量子収率も低いことが課題であった．本研究では市販品で入手な出発物質を用いて，わずか2工程で対称ポリアザ[5]-[9]ヘリセンを合成した．それらの光物性を評価したところ非常に高い量子収率，あるいは円偏光発光特性を示した．本合成を応用することにより，さらに優れた円偏光発光特性を有する材料の開発へ応用できることが示唆された．
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Report
(5 results)
Research Products
(16 results)
