• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to project page

2023 Fiscal Year Annual Research Report

Strategic Exploration of Quinoline-Based Materials

Research Project

Project/Area Number 22K14670
Research InstitutionKeio University

Principal Investigator

XU Wei  慶應義塾大学, 薬学部(芝共立), 助教 (80869272)

Project Period (FY) 2022-04-01 – 2024-03-31
KeywordsTEtraQuinoline / TEQ / quinoline / In2Q2 / macrocyclic compounds
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.

  • Research Products

    (6 results)

All 2024 2023

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (1 results)

  • [Journal Article] Recent Advances in Quinoline-Based Macrocycles: Synthesis, Properties, and Applications in Catalytic Reactions2024

    • Author(s)
      Xu Wei、Kumagai Naoya
    • Journal Title

      Synthesis

      Volume: 56 Pages: A~J

    • DOI

      10.1055/s-0042-1751545

    • Peer Reviewed
  • [Journal Article] In2Q2: A New Entry of 16‐Membered Tetraazamacrocycle Concatenating Indole and Quinoline Units2024

    • Author(s)
      Kihara Kazuki、Kobayashi Toi、Xu Wei、Kumagai Naoya
    • Journal Title

      Chemistry - A European Journal

      Volume: 30 Pages: e202304176

    • DOI

      10.1002/chem.202304176

    • Peer Reviewed
  • [Journal Article] Chemoselective Catalytic Dehydrogenation of Benzylic Amines Driven by the TEtraQuinoline/FeCl2 Complex2023

    • Author(s)
      Nishiwaki Mizuki、Xu Wei、Kumagai Naoya
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 12 Pages: e202300261

    • DOI

      10.1002/ajoc.202300261

    • Peer Reviewed
  • [Journal Article] A brief introduction to highly symmetric N-heteroarene-based macrocycles2023

    • Author(s)
      Xu Wei、Kumagai Naoya
    • Journal Title

      Tetrahedron

      Volume: 141 Pages: 133512~133512

    • DOI

      10.1016/j.tet.2023.133512

    • Peer Reviewed
  • [Journal Article] Azo-tagged C4N4 fluorophores: unusual overcrowded structures and their application to fluorescent imaging2023

    • Author(s)
      Kohei Miki、Takizawa Naoki、Tsutsumi Ryosuke、Xu Wei、Kumagai Naoya
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 21 Pages: 2889~2893

    • DOI

      10.1039/D3OB00049D

    • Peer Reviewed
  • [Presentation] Design of Novel Quinoline-based Macrocyclic Compounds2023

    • Author(s)
      Wei Xu, Kazuki Kihara, Haru Nonaka, Ryota Yagami, Ayami Takeda, Shogo Tashiro, Naoya Kumagai
    • Organizer
      日本化学会 第104春季年会

URL: 

Published: 2024-12-25  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi