2022 Fiscal Year Annual Research Report
Development of base-metal-catalyzed reactions applicable for new design of organic semiconductor materials
| Project/Area Number |
21J22172
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| Allocation Type | Single-year Grants |
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| Research Institution | The University of Tokyo |
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Principal Investigator |
陳 夢青 東京大学, 理学系研究科, 特別研究員(DC1)
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| Project Period (FY) |
2021-04-28 – 2024-03-31
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| Keywords | iron / tetra-annulation / spiro |
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| Outline of Annual Research Achievements |
In previous study I learned in the presence of FeCl2 and PPh3 as catalyst, magnesium/LiCl as a reductant and 1,2-dichloropropane as a mild oxidant, reaction occurred via an organometallic intermediate whereas the stained 1,4-dihydropentalene framework was formed. Then I extended the synthesis for more conjugated dithiophenes using iron-catalyzed tandem tetra-annulation strategy with much higher level of HOMO energy. Besides, well-developed iron-catalyzed annulative carbomagnesiation method was found to be highly applicable for synthesizing derivatized 1H-indenes, dihydro-s-indacenes, and carbon-bridged oligo p-phenylenevinylene congeners with spiro centers, which suggests us prospective work to construct an extended 1,4-dihydropentalene framework with multi-spiro-centers.
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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
An entirely flat, strained, and chemically stable 1,4-dihydropentalene framework represents the core structure of oligophenylenevinylene systems first developed by applicant’s lab for optoelectronic materials research. During the last year study, the applicant has established a method to construct this strained skeleton in a single step using iron, which exists abundantly on the earth, as a catalyst in a tandem manner providing an expeditious access to a series of fused thiophene-containing molecules (CTV) having a narrow band gap further developed for utilization in near-infrared photodetector device.
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| Strategy for Future Research Activity |
based on this year's study, further functionalization of new class of COPVs and CTV has been conducted. Furthermore, multiple-cyclization in one-pot synthesis was also investigated to extend the length of oligophenylenevinylene systems. Therefore, the future plan would be apply this iron-catalyzed multi-annulation strategy to construct the multi-spiro-centered large π-conjugated system. Besides NMR measurement, XRD analysis, thermal, photochemical and electrochemical properties will be evaluated for all newly made compounds.
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Research Products
(5 results)
