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Two-dimensional sheets with front and back faces constructed from rim-differentiated regular polygonal macrocyclic compounds

Research Project

Project/Area Number 22K19063
Research Category

Grant-in-Aid for Challenging Research (Exploratory)

Allocation TypeMulti-year Fund
Review Section Medium-sized Section 35:Polymers, organic materials, and related fields
Research InstitutionKyoto University

Principal Investigator

Ogoshi Tomoki  京都大学, 工学研究科, 教授 (00447682)

Project Period (FY) 2022-06-30 – 2024-03-31
Project Status Completed (Fiscal Year 2023)
Budget Amount *help
¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Fiscal Year 2023: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Fiscal Year 2022: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Keywordsピラー[n]アレーン / 二面性 / 二次元シート / 二分子膜 / 脂質二分子膜 / ヘキサゴナルパッキング / 気-水界面 / 二次元超分子シート / ホスト-ゲスト錯体 / 非対称 / 基板 / 空間
Outline of Research at the Start

立体的で対称性に優れた芳香族分子を用いることで、横方向への集積化による二次元超分子シートが開発され、その物性・機能に注目が集まっている。我々が合成に初めて成功した環状分子「ピラー[n]アレーン」も、立体的で正多角柱構造の芳香族分子であることから、二次元超分子シートを形成する。また最近、上下面に異なる置換基を導入した二面性ピラー[n]アレーンの合成が可能となった。本研究では、二面性ピラー[n]アレーンを基に、更に一段上の構造概念を有する二次元超分子シートとして、これまでに例を見ない「表と裏」という面を有する二次元超分子シートを創製し、その物性と機能解明を目指す。

Outline of Final Research Achievements

Pillar[n]arenes, which were firstly reported by our group, are cyclic compounds with regular polygons. Thus, they form a two-dimensional supramolecular sheets. In this study, we have created a novel two-dimensional supramolecular sheets with two different sides and have investigated their properties and functions. As a result, we found that pillar[n]arenes with hydrophobic alkyl groups on one side and cationic groups on the other side form bilayer membranes. Furthermore, when the obtained bilayer membrane was mixed with hydrophobic guest molecules using a ball mill, solubilization depending on the guest chain length was observed. Additionally, by adsorbing them onto a substrate surface, a hydrophobic surfaces were created.

Academic Significance and Societal Importance of the Research Achievements

代表的なシート状物質は、クレイがあげられる。有機カチオンをクレイ相間に挿入することで官能基化した二次元シートが得られるが、表と裏を区別して官能基化することは困難である。一原子の厚みを有するグラフェンシートにおいても、事後の表面への官能基修飾が行われているが、面選択的な修飾を行うことは同様に困難である。本研究での正多角柱分子ピラー[n]アレーンを基にした二面性二次元超分子シートは、裏表を有するという点から、これまでの二次元シートにはない一段上の構造概念を有している。これより、新構造概念の表裏を有する二次元シートという新分野を拓くことが出来た。

Report

(3 results)
  • 2023 Annual Research Report   Final Research Report ( PDF )
  • 2022 Research-status Report
  • Research Products

    (15 results)

All 2024 2023 2022 Other

All Journal Article (7 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 7 results,  Open Access: 1 results) Presentation (7 results) (of which Int'l Joint Research: 5 results,  Invited: 7 results) Remarks (1 results)

  • [Journal Article] Exciplex Formation by Complexation of an Electron-Accepting Guest in an Electron-Donating Pillar[5]arene Host Liquid2024

    • Author(s)
      Ogoshi Tomoki、Azuma Shogo、Wada Keisuke、Tamura Yuko、Kato Kenichi、Ohtani Shunsuke、Kakuta Takahiro、Yamagishi Tada-Aki
    • Journal Title

      Journal of the American Chemical Society

      Volume: 146 Issue: 14 Pages: 9828-9835

    • DOI

      10.1021/jacs.3c14582

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Self-Inclusion Complexation of Electron-Accepting Guest into Electron-Donating Cyclic Host by Photoexcitation2024

    • Author(s)
      Wada Keisuke、Nagata Yuuya、Cui Luxia、Ono Toshikazu、Akine Shigehisa、Ohtani Shunsuke、Kato Kenichi、Fa Shixin、Ogoshi Tomoki
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 63 Issue: 26 Pages: 15324-15330

    • DOI

      10.1002/anie.202404409

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Host-guest behavior of pillar[n]arene-based supramolecular assemblies2023

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

      Trends in Chemistry

      Volume: 5 Issue: 7 Pages: 537-550

    • DOI

      10.1016/j.trechm.2023.04.004

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Room‐Temperature Ring‐Opening Polymerization of δ‐Valerolactone and ?‐Caprolactone Caused by Uptake into Porous Pillar[5]arene Crystals2022

    • Author(s)
      Kato Kenichi、Maeda Koki、Mizuno Motohiro、Nishina Yuta、Fa Shixin、Ohtani Shunsuke、Ogoshi Tomoki
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 61 Issue: 50

    • DOI

      10.1002/anie.202212874

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Real-time chirality transfer monitoring from statistically random to discrete homochiral nanotubes2022

    • Author(s)
      Fa Shixin、Shi Tan-hao、Akama Suzu、Adachi Keisuke、Wada Keisuke、Tanaka Seigo、Oyama Naoki、Kato Kenichi、Ohtani Shunsuke、Nagata Yuuya、Akine Shigehisa、Ogoshi Tomoki
    • Journal Title

      Nature Communications

      Volume: 13 Issue: 1 Pages: 7378-7378

    • DOI

      10.1038/s41467-022-34827-z

    • Related Report
      2022 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] A Twisted Chiral Cavitand with 5-Fold Symmetry and Its Length-Selective Binding Properties2022

    • Author(s)
      Shi Tan-Hao、Nagata Yuuya、Akine Shigehisa、Ohtani Shunsuke、Kato Kenichi、Ogoshi Tomoki
    • Journal Title

      Journal of the American Chemical Society

      Volume: 144 Issue: 51 Pages: 23677-23684

    • DOI

      10.1021/jacs.2c11225

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Host-Guest chemistry based on solid-state pillar[n]arenes2022

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

      Coordination Chemistry Reviews

      Volume: 462 Pages: 214503-214503

    • DOI

      10.1016/j.ccr.2022.214503

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Presentation] Supramolecular Assemblies and Systems Based on Pillar-Shaped Macrocyclic Compounds "Pillar[n]arenes"2023

    • Author(s)
      Tomoki Ogoshi
    • Organizer
      National Taiwan University, Hosted by Prof. Yi-Tsu Chan, Taipei, Taiwan
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Supramolecular Assemblies and Systems Based on Pillar-Shaped Macrocyclic Compounds “Pillar[n]arenes”2023

    • Author(s)
      Tomoki Ogoshi
    • Organizer
      Westlake University, Hosted by Prof. Zhichang Liu, Hangzhou, China
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Supramolecular Assemblies and Systems Based on Pillar-Shaped Macrocyclic Compounds “Pillar[n]arenes”2023

    • Author(s)
      Tomoki Ogoshi
    • Organizer
      Zhejiang University, Hosted by Prof. Ming Liu, Hangzhou, China
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 正多角柱環状分子「ピラー[n]アレーン」を基にした分子空間化学2023

    • Author(s)
      生越友樹
    • Organizer
      化学系学協会北海道支部2023年冬季研究発表会
    • Related Report
      2022 Research-status Report
    • Invited
  • [Presentation] ピラーアレーンを基盤とする分子空間材料2022

    • Author(s)
      生越友樹
    • Organizer
      CSJフェスタ「環状分子が創り出す驚きの材料科学」
    • Related Report
      2022 Research-status Report
    • Invited
  • [Presentation] Chiral Supramolecular Assemblies and Systems Based on Pillar[n]arenes2022

    • Author(s)
      Tomoki Ogoshi
    • Organizer
      JSPS Core-to-Core Program symposium “Intelligence in Organic Materials”
    • Related Report
      2022 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Pillar-Shaped Macrocyclic Compounds “Pillar[n]arenes”: from Simple Molecular Receptors to Bulk Supramolecular Assemblies2022

    • Author(s)
      Tomoki Ogoshi
    • Organizer
      The 15th International Symposium on Organic Reactions, College of Science
    • Related Report
      2022 Research-status Report
    • Int'l Joint Research / Invited
  • [Remarks] 生越研究室

    • URL

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

    • Related Report
      2023 Annual Research Report 2022 Research-status Report

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Published: 2022-07-05   Modified: 2025-01-30  

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