Development of base-metal-catalyzed reactions applicable for new design of organic semiconductor materials
Project/Area Number |
22KJ0667
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Project/Area Number (Other) |
21J22172 (2021-2022)
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Research Category |
Grant-in-Aid for JSPS Fellows
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Allocation Type | Multi-year Fund (2023) Single-year Grants (2021-2022) |
Section | 国内 |
Review Section |
Basic Section 33020:Synthetic organic chemistry-related
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Research Institution | The University of Tokyo |
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) |
2023-03-08 – 2024-03-31
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Project Status |
Granted (Fiscal Year 2023)
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Budget Amount *help |
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 2023: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2022: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2021: ¥800,000 (Direct Cost: ¥800,000)
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Keywords | iron / tetra-annulation / spiro / Iron / optoelectronic |
Outline of Research at the Start |
I developed environmentally benign organic synthesis using iron catalysis constructing strained complicated π-conjugated framework which provides expeditious access to a series of fused thiophene-containing molecules with high HOMO level and narrow HOMO-LUMO gap useful for narrow band gap materials.
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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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Report
(2 results)
Research Products
(13 results)