2022 Fiscal Year Final Research Report
Construction of optically-active distorted pi-conjugated systems and their properties
| Project/Area Number |
19K05422
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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 | Ehime University |
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Principal Investigator |
Uno Hidemitsu 愛媛大学, 理工学研究科(理学系), 教授 (20168735)
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| Project Period (FY) |
2019-04-01 – 2023-03-31
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| Keywords | 光学活性ピロール / 光学活性ポルフィリン / 光学活性BODIPY / 円二色性 / 円偏光発光 / HPHAC / secoHPHAC / homoHPHAC |
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| Outline of Final Research Achievements |
We have synthesized optically active bicyclooctadiene-fused pyrroles from (-)-α-phellandrene and succeeded in the selective synthesis of optically active porphyrin and BODIPY. In addition, we synthesized a benzene derivative with six dye blades of doubly (R)-α-phenethylimide-substituted phenanthrenocarbazole and succeeded the X-ray crystal structure analysis. This compound exhibited temperature-dependent circular dichromism (CD) and circularly polarized luminescence (CPL) activities, which could be explained by the tilt-torsion isomer ratios expected from VT-NMR. Moreover, perethylhomohexapyrrolohexaazacoronenes with anti-aromaticity were synthesized by acylation of perethylsecohexapyrrolohexaazacoronene and their physical properties were elucidated.
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| Free Research Field |
有機化学
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| Academic Significance and Societal Importance of the Research Achievements |
本申請の研究においてはじめて光学活性基が縮環したピロールの合成ができた。このピロールから光学活性ポルフィリンや位置選択的に合成されたことのないベンゾ部位に複数の置換基を有するテトラベンゾポルフィリンを合成できたことは，今後の有機機能材料科学にとって大きな意義があると考えている。また，ベンゼン環に円環状に置換した色素ブレードの傾きねじれにおいて不斉補助基による制御が効率よく行え，大きなCD及びCPL活性を発現させたことは今後の有機光学材料の新しいジャンルを開くものと期待される。
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