Stereoselective synthesis and higher-order derivatization of planar chiral cyclophanes
| Project/Area Number |
23655031
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| Research Category |
Grant-in-Aid for Challenging Exploratory Research
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| Allocation Type | Multi-year Fund |
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| Research Field |
Organic chemistry
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| Research Institution | Tokyo Institute of Technology |
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Principal Investigator |
OHMORI Ken 東京工業大学, 大学院・理工学研究科, 准教授 (50282819)
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| Project Period (FY) |
2011 – 2012
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| Project Status |
Completed (Fiscal Year 2012)
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| Budget Amount *help |
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2012: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2011: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
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| Keywords | 合成有機化学 / 立体化学 / 芳香族化合物 / シクロファン / 面性不斉 / ポリフェニレン / C2対称性 / パラシクロファン / 面不斉 / スルホキシド |
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| Research Abstract |
This syntheses of C_2-symmetric enantiomerically pure polyparacyclophane derivatives were achieved by Suzuki-Miyaura coupling method, where the synthesis of these C_2 -symmetrical paracyclophanes was based on the hydrogen-bond controlling strategy by using styryl sulfoxide derivatives. Bistriflates, derived from dihydroquinone derivative of monomeric cyclophanes, were used as building blocks for their oligomer synthesis. Incorporation of phenyl spacer to sustain π-conjugation was successful, giving a heptaphenylene derivative. The structure was confirmed by single crystal X-ray analysis, revealing its linear structure. UV-vis and CD spectra of the compound suggested a helical conformation of thepolyphenylene skeleton in organic solvents, such as chloroform.
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Report
(3 results)
Research Products
(10 results)
