| Project/Area Number |
22K14670
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| Research Category |
Grant-in-Aid for Early-Career Scientists
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| Allocation Type | Multi-year Fund |
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| Review Section |
Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
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| Research Institution | Keio University |
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Principal Investigator |
XU Wei 慶應義塾大学, 薬学部(芝共立), 助教 (80869272)
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| Project Period (FY) |
2022-04-01 – 2024-03-31
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| Project Status |
Completed (Fiscal Year 2023)
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| Budget Amount *help |
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2023: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Fiscal Year 2022: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
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| Keywords | TEtraQuinoline / TEQ / quinoline / In2Q2 / macrocyclic compounds / metal complex / saddle shape / macrocycle / tetradentate / oligomer / catalysis / fluorescence |
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| Outline of Research at the Start |
This project aims at design and synthesis of novel quinoline-based materials for supramolecular chemistry and catalysis developments. The π-wall materials armed with pyridinic nitrogens will exhibit particular physical and chemical properties in molecular recognition and catalysis.
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| Outline of Final Research Achievements |
In this study, we designed and synthesized a cyclic quinoline tetramer, TEtraQuinoline (TEQ), which features a 16-membered ring skeleton. TEQ is an N4-type macrocyclic molecule similar to porphyrin, but it is characterized by its saddle-shaped structure and neutral nature when acting as a ligand. TEQ forms complexes with a series of transition metals (Fe2+, Co2+, Ni2+, Cu2+, Zn2+, and Pd2+), as confirmed by X-ray crystallography. A TEQ/Fe(II) complex exhibited high catalytic activity, promoting the dehydrogenation of benzylamine with catalyst amounts as low as 0.1 mol%. TEQ also demonstrated strong fluorescence upon protonation and in the presence of Zn(II) cations, indicating potential applications as structurally robust probes for acids and zinc. Additionally, we synthesized a novel nitrogen macrocyclic ligand, In2Q2, consisting of two indoles (In) and two quinolines (Q). Its saddle-shaped structure and formation of Zn complexes have been confirmed.
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| Academic Significance and Societal Importance of the Research Achievements |
The cyclic quinoline tetramer TEQ is a novel nitrogen ligand that can be regarded as a non-planar porphyrinoid. It coordinates with a range of transition metals, showing great potential in catalysis, including asymmetric transformations. Additionally, it shows promise as a fluorescent material.
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