| Project/Area Number |
17550047
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Tokyo Kasei Gakuin University |
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Principal Investigator |
YOKOYAMA Yayoi Tokyo Kasei Gakuin University, Department of Home Economics, Professor (70142263)
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| Co-Investigator(Kenkyū-buntansha) |
YOKOYAMA Yasushi Yokohama National University, Department of Advanced Materials Chemistry, Graduate School of Engineering, Professor (60134897)
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| Project Period (FY) |
2005 – 2007
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| Project Status |
Completed (Fiscal Year 2007)
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| Budget Amount *help |
¥3,810,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥210,000)
Fiscal Year 2007: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2006: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2005: ¥2,200,000 (Direct Cost: ¥2,200,000)
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| Keywords | photochromism / helicene / diarylethene / diastereoselectivity / benzothiophene / perfluorocyclopentene / repulsion / methoxyl / 光学活性 / ビナフトール / フォトクロミズム / へリックス / 旋光度 / 量子収率 / ヘリセン / ジアステレオ選択的 / アリリックストレイン / 光閉環反応 |
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| Research Abstract |
Helicenes are known to show large specific optical rotation. In order to induce a large change in optical rotation, a diastereoselective photochromic reaction should take place. We chose to induce a diastereoselective photochromic reaction with a simple chiral auxiliary attached to the ring-closing hexatriene moiety. Then, we synthesized six chiral helicenoid diarylethenes having the aromatic group connected to perfluorocyclipentene at C-3 or C-2. We examined the photochemical behaviors of these six molecules, especially about the diastereoselectivity in photochromism. In the course of these investigations, we could gain the useful inspection about the relation between the diastereoselectivity and the substitution groups (methoxyl group and methoxymethoxyl group) in diarylethenes to obtain large optical rotation changes in photochromism. That is, we found the steric and electronic repulsion between two substitution groups and the electronic repulsion between the methoxyl group and benzothiophen moiety in these molecules were important.
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