2016 Fiscal Year Annual Research Report
５員環を含むＰＡＨの特異な反応性開発と高発光性π共役分子群の創製
| Project/Area Number |
16J11545
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| Research Institution | Kyoto University |
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Principal Investigator |
朝 魯門 京都大学, 工学研究科, 特別研究員(DC2)
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| Project Period (FY) |
2016-04-22 – 2018-03-31
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| Keywords | CP-PAHs / the Scholl reaction / tetracene |
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| Outline of Annual Research Achievements |
In the past one year, my research work mainly focused on synthesis, mechanism, and properties of CP-PAHs.
(1) 5,11-dinaphthyltetracene underwent the twofold Scholl cyclization and gave unsymmetrically cyclized naphthalene-fused tetracene with one pentagonal and hexagonal ring. Mechanistic study for this unique selectivity disclosed the dication pathway of the Scholl reaction.
(2) This unsymmetrically cyclized naphthalene-fused tetracene reacts with benzyne to give emissive mono-and bisadducts with unique 3D structures.
(3) Similarly, dithieno-fused CP-PAH was synthesized. Experimental and theoretical studies demonstrated that this molecule exhibits strong antiaromatic character on its pentagonal rings.
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| Current Status of Research Progress |
Current Status of Research Progress
2: Research has progressed on the whole more than it was originally planned.
Reason
Cyclic voltammetry showed that CP-PAHs like tetrabenzo-fused pyracylene and dithieno-fused CP-PAH can easily and reversibly accept up to two electrons. To gain insight into the solid-state properties and structural changes upon accepting one and two electron, lithium reduction was conducted to these compounds. The corresponding radical anion and dianion were obtained and their structures were determined by XRD analysis. For these materials and their reduced species, additional studies such as photophysical and magnetic properties as well as the solid-state packing are under investigations.
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| Strategy for Future Research Activity |
(1) Due to the high redox activity, the CP-PAHs may have potential applications in the rechargeable battery field as electrode-active materials. In the near future, I will focus on design and synthesis of a series of CP-PAHs with larger π-system and more redox abilities. Furthermore, the solid-state properties of their reduced and oxidized species will be investigated for battery applications.
(2) Based on original plan, the reactivity of these molecules will be explored for the understanding of the unique reactivity of CP-PAHs. More importantly, the thus obtained products are likely to be potential emissive materials and can be applied in the OLED field.
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