2016 Fiscal Year Final Research Report
Synthesis of pyrrole-containing polycyclic aromatic hydrocarbons with remarkable curvatures
| Project/Area Number |
26810021
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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
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| Research Institution | Kyoto University |
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Principal Investigator |
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| Project Period (FY) |
2014-04-01 – 2017-03-31
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| Keywords | 多環芳香族炭化水素 / 酸化的縮環反応 / 芳香族性 / 湾曲化合物 |
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| Outline of Final Research Achievements |
Tetrabenzotetraaza[8]circulene was obtained by "fold-in" type oxidative fusion reaction of ortho-phenylene bridged cyclic tetrapyrrole in high yield. This planar aromatic molecule exhibited bright blue emission with a quite small Stokes shift. The optical property was tunable by sequential alkylations of the outer-pointing NH groups.
With this new synthetic method in hands, the synthesis of triazasumanene was examined. However, the same oxidative fusion reaction of cyclic tripyrrole furnished partially fused compound in low yield. The same protocol was utilized for cyclic hexapyrrole, which afforded partially fused closed-helicenes in a selective manner. Overall, the "fold-in" type fusion reaction was found to be quite sensitive to the flexibility of the cyclic precursor.
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| Free Research Field |
有機化学
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