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芳香環配位カプセルの空間修飾による超選択的テルペン環化反応

Research Project

Project/Area Number 23K13760
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 34010:Inorganic/coordination chemistry-related
Research InstitutionTokyo Institute of Technology

Principal Investigator

CATTI LORENZO  東京工業大学, 科学技術創成研究院, 助教 (50873478)

Project Period (FY) 2023-04-01 – 2026-03-31
Project Status Granted (Fiscal Year 2023)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2025: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2024: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2023: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordsfunctionalized capsule / functionalized ligand / heterocapsule / テルペン環化反応
Outline of Research at the Start

Preparation of novel ligands with covalently attached acid functionalities.
Formation of nanosized M2L4 coordination capsules via self-assembly of these ligands in the presence of metal ions (Pd2+ or Pt2+).
Cyclization of linear terpene substrates inside the obtained capsules via protonation in water.

Outline of Annual Research Achievements

The synthesis of a new bent endo-functionalized bispyridine ligand was achieved. During the synthesis the convex-selective deprotection of the alkoxy groups was successfully performed. The ligand features an internal OAc or OH substituent. Combination of this ligand with metal ions resulted in the formation of an internally functionalized coordination capsule, as indicated by NMR analysis. The formed capsule is believed to contain both internal OH and OAc functionalities, since a mixture of the functionalized ligand was used. Formation of such heterocapsules is an important step toward mimicking the active centers of natural enzymes.

Current Status of Research Progress
Current Status of Research Progress

2: Research has progressed on the whole more than it was originally planned.

Reason

The synthesis of the ligand was achieved without major problems. Importantly, the obtained OH functionalized ligand can likely be converted into other functionalized ligands, e.g. ones containing acidic groups. Additionally, current NMR data indicates formation of otherwise difficult-to-obtain heterocapsules, which might prove valuable for the selective recognition of biomolecules in water.

Strategy for Future Research Activity

First the purification of the obtained ligand will be finalized, since the current ligand is obtained as a mixture of OH- and OAc-functionalized ligands. With the separated ligands in hand, we will first study the formation of homocapsules and their selective guest-uptake abilities. Next we will study the selective formation of e.g. 2+2 heterocapsules using a mixture of functionalized and unfunctionalized ligands. Selective formation will be attempted using template guest molecules or using functionalized ligands with sterically bulky substituents.

Report

(1 results)
  • 2023 Research-status Report
  • Research Products

    (4 results)

All 2024

All Journal Article (1 results) (of which Peer Reviewed: 1 results) Presentation (3 results) (of which Int'l Joint Research: 3 results)

  • [Journal Article] Facile access to pyridinium-based bent aromatic amphiphiles: nonionic surface modification of nanocarbons in water2024

    • Author(s)
      Catti Lorenzo、Aoyama Shinji、Yoshizawa Michito
    • Journal Title

      Beilstein Journal of Organic Chemistry

      Volume: 20 Pages: 32-40

    • DOI

      10.3762/bjoc.20.5

    • Related Report
      2023 Research-status Report
    • Peer Reviewed
  • [Presentation] 芳香環カプセルの空間修飾を目指した新配位子設計2024

    • Author(s)
      村松快飛・遠藤匡哉・Lorenzo Catti・吉沢道人
    • Organizer
      日本化学会 第104回 春季年会
    • Related Report
      2023 Research-status Report
    • Int'l Joint Research
  • [Presentation] 高密度アルキル空間を持つ芳香環ミセルの性質解明2024

    • Author(s)
      遠藤匡哉・青山慎治・Lorenzo Catti・吉沢道人
    • Organizer
      日本化学会 第104回 春季年会
    • Related Report
      2023 Research-status Report
    • Int'l Joint Research
  • [Presentation] 凹部に極性官能基を導入したアントラセン二量体の合成2024

    • Author(s)
      菊地悠太・青山慎治・Lorenzo Catti・吉沢道人
    • Organizer
      日本化学会 第104回 春季年会
    • Related Report
      2023 Research-status Report
    • Int'l Joint Research

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Published: 2023-04-13   Modified: 2024-12-25  

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