2023 Fiscal Year Annual Research Report
Strategic Exploration of Quinoline-Based Materials
| Project/Area Number |
22K14670
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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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| Keywords | TEtraQuinoline / TEQ / quinoline / In2Q2 / macrocyclic compounds |
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| Outline of Annual Research Achievements |
This study focuses on the design and synthesis of macrocyclic compounds based on quinoline units, and explores their applications as nitrogen ligands in organometallic chemistry and catalysis. In our previous work, we have developed TEtraQuinoline (TEQ) with a saddle-shaped structure and four inward sp2 nitrogens, which could be regarded as a non-planar warped porphyrinoid..
This year, we focused on the catalytic application of TEQ-metal complexes, and developed dehydrogenation of benzylic amines in the presence of TEQ/FeCl2 complex and peroxides. Various primary and secondary amine substrates are compatible, yielding the imine products in moderate to good yields with turnover numbers up to 2250. Chemoselective deprotection of the N-Bn group over the N-Cbz group was achieved, highlighting the practicality of this methodology as a deprotection protocol complementary to reductive conditions promoted by Pd catalysis. In addition, we developed a new saddle-shaped tetradentate nitrogen ligand In2Q2, which consists of two indole (In) and two quinoline (Q) units. In2Q2 can coordinate with Zn2+ to form a neutral Zn complex, acting as a dianionic type ligand. Fluorescence of In2Q2 was observed both in the solution phase and the solid state, with emission maxima ranging from 456-527 nm depending on different substituents.
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