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Enantio-selective transportation of natural small chiral molecules via discrete access-controllable nanotubes based on pillararene

Research Project

Project/Area Number 21K14612
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
Research InstitutionKyoto University

Principal Investigator

FA SHIXIN  京都大学, 工学研究科, 特定助教 (40835922)

Project Period (FY) 2021-04-01 – 2022-03-31
Project Status Discontinued (Fiscal Year 2021)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2022: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2021: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
KeywordsPillar[5]arene / Chirality / Molecular Tube / Ionic Interaction / Assembly / self-assemblies / pillararenes / artificial channels / chirality / nanotubes
Outline of Research at the Start

Artificial channels with selectivity for natural molecules has becoming attractive for a long time because of the significance of the related life processes. However, this subject remains a challenging field due to the sophisticated molecular design and low efficiency. Here, the applicant will use simple assembled structures, pillar[5]arene-based discrete nanotubes, as artificial channels for amino acids and monosaccarides, as pillararenes are host molecules for them. Optical and directional control of the transportation behaviors will also be studied by modifying the molecular structures.

Outline of Annual Research Achievements

Selectively transporting hydrophilic natural molecules with chirality through artificial channels is of crucial importance. However, this work is challenging due to the sophisticated molecular design and standing low efficiency. To achieve this goal, the construction of channels with chiral information is the primary task.
Taking advantage of the controllable planar-chiral properties of pillar[n]arenes, we started the project with a rim-differentiated pillar[5]arene bearing stereogenic centers on one rim and benzoic acids on the other rim. An diastereomeric excess of the pillar[5]arene was produced through the host-guest interaction with achiral linear guests. The trimeric nanotubes with specific helicity and stability were synthesized through the ionic interaction of the pre-regulated rim-differentiated pillar[5]arene with an amino pillar[5]arene.
Another strategy on construction of helical trimeric nanochannels was also practiced. An acidic rim-differentiated pillar[5]arene without stereogenic centers was isolated into two enantiomers firstly, and interacted with the amino pillar[5]arene to produce enantiomeric nanochannels. The constructed channels possessed pure left- and right-handed helicity.
These trimeric nanotubes were expected to work as artificial channels enabling enantio-selective transportation of natural small chiral molecules, because previous work has revealed the enantio-selective recognition of pillar[5]arenes.

Report

(1 results)
  • 2021 Annual Research Report
  • Research Products

    (6 results)

All 2021 Other

All Int'l Joint Research (1 results) Journal Article (3 results) (of which Peer Reviewed: 3 results,  Open Access: 2 results) Presentation (1 results) Remarks (1 results)

  • [Int'l Joint Research] University of Montpellier(フランス)

    • Related Report
      2021 Annual Research Report
  • [Journal Article] Pre-regulation of the planar chirality of pillar[5]arenes for preparing discrete chiral nanotubes2021

    • Author(s)
      Fa Shixin、Adachi Keisuke、Nagata Yuuya、Egami Kouichi、Kato Kenichi、Ogoshi Tomoki
    • Journal Title

      Chemical Science

      Volume: 12 Issue: 10 Pages: 3483-3488

    • DOI

      10.1039/d1sc00074h

    • NAID

      120006997053

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Reversible “On/Off” Chiral Amplification of Pillar[5]arene Assemblies by Dual External Stimuli2021

    • Author(s)
      Fa Shixin、Mizobata Masayuki、Nagano Shusaku、Suetsugu Kota、Kakuta Takahiro、Yamagishi Tada-aki、Ogoshi Tomoki
    • Journal Title

      ACS Nano

      Volume: 15 Issue: 10 Pages: 16794-16801

    • DOI

      10.1021/acsnano.1c06975

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Discrete and Continuous One-Dimensional Channels Based on Pillar[n]arenes2021

    • Author(s)
      Kato Kenichi、Ohtani Shunsuke、Fa Shixin、Ogoshi Tomoki
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 94 Issue: 10 Pages: 2319-2328

    • DOI

      10.1246/bcsj.20210243

    • NAID

      130008117246

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Presentation] Planar chirality induction of pillararenes and chiral nanotube formation2021

    • Author(s)
      Shixin Fa, Kouichi Egami, Suzu Akama, Kenichi Kato, Shigehisa Akine, Tomoki Ogoshi
    • Organizer
      18th Symposium on Host-Guest and Supramolecular Chemistry
    • Related Report
      2021 Annual Research Report
  • [Remarks] Lab Homepage

    • URL

      http://www.sbchem.kyoto-u.ac.jp/ogoshi-lab/index_en.html

    • Related Report
      2021 Annual Research Report

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Published: 2021-04-28   Modified: 2022-12-28  

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