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Development of molecular-single-crystalline-catalyst cartridges

Research Project

Project/Area Number 21K18961
Research Category

Grant-in-Aid for Challenging Research (Exploratory)

Allocation TypeMulti-year Fund
Review Section Medium-sized Section 33:Organic chemistry and related fields
Research InstitutionOsaka University

Principal Investigator

Hisaki Ichiro  大阪大学, 大学院基礎工学研究科, 教授 (90419466)

Project Period (FY) 2021-07-09 – 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: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2022: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2021: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords水素結合 / 多孔質構造体 / 単結晶 / 多孔質結晶 / ヘキサアザトリフェニレン / ジベンゾクリセン / 有機結晶 / 多孔質材料
Outline of Research at the Start

構造と物性を自由にデザインできる有機分子の特徴を生かして、有機分子を基盤とした安定な多孔質単結晶を調整し、一連の「単結晶触媒」を構築する。さらにその単結晶を、あたかもプリンターのインクカートリッジのように微少流路系に装填・交換できる「単結晶触媒カートリッジ」として展開するための要素技術開発および概念実証を目的とする。

Outline of Final Research Achievements

Isostructural porous crystals with various pore diameters can be used as a library of porous materials. However, it has been difficult to construct a such library of single-crystalline porous organic crystals with channel structures. In this study, by utilizing shape-fitted stacking of twisted π-conjugated molecules, we succeeded in constructing rigid porous organic crystals that can maintain single crystallinity after activation, even with simple hydrogen bonding dimerization of carboxy groups. These results can be used as a guideline for constructing single-crystalline porous crystals, and are expected to be applied to reaction channels using single crystals by finding conditions to control the morphology of single crystals in the future.

Academic Significance and Societal Importance of the Research Achievements

多様な分子を用いることで、チャネル空間の形状、開口サイズおよびチャネル表面の性質を必要に応じて変調させた多孔質材料が構築できるが、これまでは、十分な大きさのチャネル空間を有した「堅牢な有機結晶」を、非共有結合によって構築することは困難であり、特に同型構造をもつライブラリー構築に指針は無かった。これに対し、カルボン酸の2量化という単純な分子結合モチーフをπ共役骨格の剛直な積層構造と同時に用いるという普遍性のある手法で、十分な大きさのチャネル空間を有した「堅牢な有機結晶」を構築できた点に学術的な意義がある。

Report

(4 results)
  • 2023 Annual Research Report   Final Research Report ( PDF )
  • 2022 Research-status Report
  • 2021 Research-status Report
  • Research Products

    (35 results)

All 2024 2023 2022 2021 Other

All Int'l Joint Research (2 results) Journal Article (11 results) (of which Int'l Joint Research: 4 results,  Peer Reviewed: 11 results,  Open Access: 3 results) Presentation (19 results) (of which Int'l Joint Research: 10 results,  Invited: 7 results) Remarks (3 results)

  • [Int'l Joint Research] University of Castila La Mancha(スペイン)

    • Related Report
      2023 Annual Research Report
  • [Int'l Joint Research] University of Castilla La Mancha(スペイン)

    • Related Report
      2021 Research-status Report
  • [Journal Article] An expanded hydrogen-bonded organic framework formed by a tetrakis(terphenyl)ethene derivative2024

    • Author(s)
      Yamaguchi Mao、Tomas Mario de la Hoz、Fujiwara Ayano、Oketani Ryusei、Okubo Kohei、Oka Kouki、Tohnai Norimitsu、Douhal Abderrazzak、Hisaki Ichiro
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 97 Issue: 1

    • DOI

      10.1093/bulcsj/uoae004

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] A Hydrogen-Bonded, Hexagonally Networked, Layered Framework with Large Aperture Designed by Structural Synchronization of a Macrocycle and Supramolecular Synthon2024

    • Author(s)
      Yoshimura Hiroki、Oketani Ryusei、Naruoka Miki、Tohnai Norimitsu、Hisaki Ichiro
    • Journal Title

      Precision Chemistry

      Volume: 2 Issue: 5 Pages: 221-228

    • DOI

      10.1021/prechem.4c00019

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Structural details of carboxylic acid-based Hydrogen-bonded Organic Frameworks (HOFs)2023

    • Author(s)
      Suzuki Yuto、Hisaki Ichiro
    • Journal Title

      Polymer Journal

      Volume: 56 Issue: 1 Pages: 1-16

    • DOI

      10.1038/s41428-023-00840-2

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Photocyclization reaction and related photodynamics in the photoproducts of a tetraphenylethylene derivative with bulky substituents: unexpected solvent viscosity effect2023

    • Author(s)
      de la Hoz Tomas Mario、Yamaguchi Mao、Cohen Boiko、Hisaki Ichiro、Douhal Abderrazzak
    • Journal Title

      Physical Chemistry Chemical Physics

      Volume: 25 Issue: 28 Pages: 18874-18888

    • DOI

      10.1039/d3cp01295f

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Single Crystalline, Non-stoichiometric Cocrystals of Hydrogen-Bonded Organic Frameworks2023

    • Author(s)
      Taito Hashimoto, Ryusei Oketani, Masaki Nobuoka, Shu Seki, Ichiro Hisaki
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 62 Issue: 1

    • DOI

      10.1002/anie.202215836

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Isomeric Effect of Naphthyl Spacers on Structures and Properties of Isostructural Porous Crystalline Frameworks2023

    • Author(s)
      Yuto Suzuki, Mao Yamaguchi, Ryusei Oketani, Ichiro Hisaki
    • Journal Title

      Mater. Chem. Front.

      Volume: 7 Issue: 1 Pages: 106-116

    • DOI

      10.1039/d2qm01091g

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Geometrically Mismatched Hydrogen-bonded Framework Composed of Tetratopic Carboxylic Acid2022

    • Author(s)
      Zhuxi Yang, Taito Hashimoto, Ryusei Oketani, Takayoshi Nakamura, Ichiro Hisaki
    • Journal Title

      Chem. Eur. J.

      Volume: 28 Issue: 50

    • DOI

      10.1002/chem.202201571

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Slip-Stacking of Benzothiadiazole Can Provide a Robust Structural Motif for Porous Hydrogen-bonded Organic Frameworks2022

    • Author(s)
      Zhuxi Yang, Akinori Saeki, Asato Inoue, Ryusei Oketani, Kazuhide Kamiya, Shuji Nakanishi, Takayoshi Nakamura, Ichiro Hisak
    • Journal Title

      Cryst. Growth Des.

      Volume: 22 Issue: 7 Pages: 1172-1179

    • DOI

      10.1021/acs.cgd.2c00420

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] Quinoxaline-annelated Hexadehydro[12]annulene: Use of A New Building Block to Construct a Hydrogen-bonded Hexagonal Molecular Network2022

    • Author(s)
      Mayu Kobayashi, Haruka Kubo, Ryusei Oketani, Ichiro Hisaki
    • Journal Title

      CrystEngComm

      Volume: 24 Issue: 28 Pages: 5036-5040

    • DOI

      10.1039/d2ce00676f

    • Related Report
      2022 Research-status Report
    • Peer Reviewed
  • [Journal Article] A Proton Conductive Porous Framework of an 18-Crown-6-Ether Derivative Networked by Rigid Hydrogen Bonding Modules2022

    • Author(s)
      Xin Chen, Rui-Kang Huang, Kiyonori Takahashi, Shin-ichiro Noro, Takayoshi Nakamura, Ichiro Hisaki
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 61 Issue: 45

    • DOI

      10.1002/anie.202211686

    • Related Report
      2022 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] HOFs Built from Hexatopic Carboxylic Acids: Structure, Porosity, Stability, and Photophysics2022

    • Author(s)
      di Nunzio Maria Rosaria、Suzuki Yuto、Hisaki Ichiro、Douhal Abderrazzak
    • Journal Title

      International Journal of Molecular Sciences

      Volume: 23 Issue: 4 Pages: 1929-1929

    • DOI

      10.3390/ijms23041929

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Presentation] Structural transformation of hydrogen-bonded organic frameworks based on pyrene derivative.2023

    • Author(s)
      橋本泰利、桶谷龍成、久木一朗
    • Organizer
      第72回高分子学会年次大会
    • Related Report
      2023 Annual Research Report
  • [Presentation] A layered assembly of hydrogen-bonded hexagonal low-density network based on a macrocyclic molecule2023

    • Author(s)
      吉村大暉、桶谷龍成、久木一朗
    • Organizer
      The 13th SPSJ International Polymer Conference
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Construction of hydrogen-bonded, ladder-shaped, porous structures using a low-symmetric tricarbpxylic acids2023

    • Author(s)
      田中那樹、桶谷龍成、久木一朗
    • Organizer
      The 13th SPSJ International Polymer Conference
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Construction of light-responsive hydrogen-bonded supramolecular networks based on dimethyldihydrobenzo[e]pyrene derivatives2023

    • Author(s)
      糟谷昂毅、桶谷龍成、久木一朗
    • Organizer
      The 13th SPSJ International Polymer Conference
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Construction of Non-stoichiometric Cocrystals of Hydrogen-bonded Organic Framework Based on Pyrene/hydropyrene System2023

    • Author(s)
      橋本泰利、桶谷龍成、久木一朗
    • Organizer
      IUCr 2023
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Deciphering the Effect of Pore Size on Transformation of Hydrogen-bonded Organic Frameworks2023

    • Author(s)
      久保遥、桶谷龍成、久木一朗
    • Organizer
      IUCr 2023
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] A Structural Quest for Porous Molecular Crystals2023

    • Author(s)
      久木一朗
    • Organizer
      2023 Taiwan-Japan Bilateral Workshop
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] π共役電子系化合物のカルボン酸誘導体が織りなす分子集合2023

    • Author(s)
      久木一朗
    • Organizer
      第16回有機π電子系シンポジウム
    • Related Report
      2023 Annual Research Report
    • Invited
  • [Presentation] Porous crystalline frameworks constructed through intermolecular hydrogen bonds of carboxy groups2023

    • Author(s)
      久木一朗
    • Organizer
      Kyoto Advanced Porous Science Symposiu
    • Related Report
      2022 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 水素結合の指向性を利用した結晶性多孔質有機材料の創製2022

    • Author(s)
      久木一朗
    • Organizer
      第71回高分子学会年次大会
    • Related Report
      2022 Research-status Report
    • Invited
  • [Presentation] 水素結合の指向性を利用した結晶性多孔質有機材料の創製2022

    • Author(s)
      久木一朗
    • Organizer
      錯体若手の会 夏の学校2022
    • Related Report
      2022 Research-status Report
    • Invited
  • [Presentation] 水素結合で分子をつなげた多孔質構造体の構造・機能設計2022

    • Author(s)
      久木一朗
    • Organizer
      M&BE新分野開拓研究会2022
    • Related Report
      2022 Research-status Report
    • Invited
  • [Presentation] Porous Organic Crystals Constructed with Directional Hydrogen Bonds2022

    • Author(s)
      久木一朗
    • Organizer
      POPs 2022 International Symposium on Porous Organic Polymers
    • Related Report
      2022 Research-status Report
    • Int'l Joint Research
  • [Presentation] Construction of hydrogen-bonded organic frameworks with naphthoic acid groups and its structural transition behavior2022

    • Author(s)
      鈴木 悠斗、桶谷 龍成、久木 一朗
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] 水素結合の組み換えをともなう多孔質構造体の単結晶構造転移機構2022

    • Author(s)
      久保 遥、桶谷龍成、久木一朗
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] キラル空間の構築を志向した非対称非平面π共役分子の合成2022

    • Author(s)
      田中 那樹、桶谷 龍成、久木 一朗
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] 低密度水素結合フレームワークの構築を志向したフェニレンエチニレン大環状分子の合成2022

    • Author(s)
      吉村 大暉、鈴木悠斗、桶谷龍成、久木一朗
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] Stimuli-responsive hydrogen-bonded organic frameworks2021

    • Author(s)
      Ichiro Hisaki
    • Organizer
      PacifiChem2021
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Construction of hydrogen-bonded organic frameworks with different stacking manner based on dibenzo[g,p]chrysene derivative2021

    • Author(s)
      鈴木 悠斗、藤内 謙光、久木 一朗
    • Organizer
      PacifiChem2021
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research
  • [Remarks] 研究室HP

    • URL

      https://www.chem.es.osaka-u.ac.jp/mac/

    • Related Report
      2023 Annual Research Report
  • [Remarks] 研究室HP

    • URL

      http://www.chem.es.osaka-u.ac.jp/mac

    • Related Report
      2022 Research-status Report
  • [Remarks] 研究室ホームページ

    • URL

      http://www.chem.es.osaka-u.ac.jp/mac/

    • Related Report
      2021 Research-status Report

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Published: 2021-07-13   Modified: 2025-01-30  

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