2014 Fiscal Year Final Research Report
Construction and Search for the Function of Polycyclic Hydrocarbon Derivatives with Antiaromaticity
| Project/Area Number |
25870112
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Organic chemistry
Functional solid state chemistry
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| Research Institution | Gunma University |
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Principal Investigator |
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| Project Period (FY) |
2013-04-01 – 2015-03-31
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| Keywords | 共役炭化水素 / 反芳香族性 / ペンタレン / 電気化学 / X線結晶構造解析 / 量子化学計算 |
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| Outline of Final Research Achievements |
Various antiaromatic benzo- and naphthopentalene derivatives were synthesized by nucleophilic addition of lithium acetylide to the corresponding pentalenequinones followed by Tin(II)chloride, 2-hydrate-mediated reduction, and their structure-property relationships were established by various spectroscopic studies, X-ray crystallographic analyses, and quantum chemical calculations. For example, their antiraromaticity were assessed by calculations of NICS values, and it was found that the annulated aromatic ring to the pentalene moiety and the annulation pattern remarkably affect the antiaromaticity of pentalene derivatives. The substituent effects on the optoelectronic and electrochemical properties were clarified. The reactions of benzopentalenequinone derivative with donor-substituted alkynes were investigated, and fluorenone and azulenequinone derivatives were obtained via regioselective [4 + 2] and [2 + 2] cycloaddition reactions, respectively.
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| Free Research Field |
有機化学
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