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Development of Single-Crystalline Porous Frameworks of Pi-Conjugated Molecules Connected though Simple Hydrogen Bonds

Research Project

Project/Area Number 18H01966
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
Research InstitutionOsaka University (2019-2020)
Hokkaido University (2018)

Principal Investigator

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

Co-Investigator(Kenkyū-buntansha) 藤内 謙光  大阪大学, 工学研究科, 准教授 (30346184)
Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥17,550,000 (Direct Cost: ¥13,500,000、Indirect Cost: ¥4,050,000)
Fiscal Year 2020: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2019: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2018: ¥9,230,000 (Direct Cost: ¥7,100,000、Indirect Cost: ¥2,130,000)
Keywords水素結合 / 多孔質構造体 / 分子性結晶 / パイ共役分子 / 有機フレームワーク / ガス吸着 / 刺激応答 / 固体蛍光 / 多孔質材料 / カルボン酸 / 単結晶 / 結晶工学 / 多孔性材料 / 水素結合性有機フレームワーク / 非平面パイ共役炭化水素 / 外部刺激応用性 / ヘキサアザトリフェニレン / 永続的多孔性 / 刺激応答性 / 有機多孔質材料 / 共役パイ電子系 / 単結晶性 / 超分子化学
Outline of Final Research Achievements

Porous frameworks composed of organic molecules have been of attractive substantial interest from viewpoints of functional host-guest systems and optelectronic materials because of tunability of molecular structures and properties. In this project, we successfully constructed various hydrogen-bonded organic frameworks based on organic molecules possessing a rigid pi-conjugated skeleton carboxy groups that is one of the simplest and the most fundamental hydrogen bonding group. The resultant HOFs exhibit (1) single crystallinity which allows to characterize precise molecular arrangements by X-ray crystallography, (2) rigidity of the frameworks with permanent porosity and flexibility to response external stimuli, and (3) high designability to achieve the structures was they were designed. These results contribute to progress of chemistry on porous molecular crystals.

Academic Significance and Societal Importance of the Research Achievements

水素結合のような弱い分子間相互作用によって分子を集積させて構築した多孔質構造体は、構造が弱く内部に大きな空孔を保持することはできない、というのがこれまでの一般的な認識であった。これに対して我々は、複数の水素結合基を幾何構造や対称性に配慮して剛直なパイ共役分子に導入すれば、内部に大きな空孔を保持できるだけの十分な強度を有する分子集積体を体系的に構築できることを示した。以上の結果は、様々な用途に応用されている多孔質材料の新たな側面を基礎と応用の両方の観点から照らし出すものである。特に近年、特定種の気体に対して、選択的に吸着・貯蔵・反応できる多孔質材料が求められており、本研究がこれに貢献できる。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Annual Research Report
  • 2018 Annual Research Report
  • Research Products

    (47 results)

All 2021 2020 2019 2018 Other

All Int'l Joint Research (3 results) Journal Article (19 results) (of which Int'l Joint Research: 6 results,  Peer Reviewed: 19 results,  Open Access: 7 results) Presentation (20 results) (of which Int'l Joint Research: 7 results,  Invited: 8 results) Book (1 results) Remarks (4 results)

  • [Int'l Joint Research] Universidad de Castilla La Mancha(スペイン)

    • Related Report
      2020 Annual Research Report
  • [Int'l Joint Research] Universidad de Castilla-La Mancha/Universitat Autónoma de Barcelona(スペイン)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] Universidad de Castilla-La Mancha(スペイン)

    • Related Report
      2018 Annual Research Report
  • [Journal Article] A hydrogen-bonded organic framework based on redox-active tri(dithiolylidene)cyclohexanetrione2021

    • Author(s)
      Shivakumar Kilingaru I.、Noro Shin-ichiro、Yamaguchi Yuna、Ishigaki Yusuke、Saeki Akinori、Takahashi Kiyonori、Nakamura Takayoshi、Hisaki Ichiro
    • Journal Title

      Chemical Communications

      Volume: 57 Issue: 9 Pages: 1157-1160

    • DOI

      10.1039/d0cc07776c

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Redox-induced reversible [2 + 2] cycloaddition of an etheno-fused diporphyrin2021

    • Author(s)
      Miyagawa Kazuya、Hisaki Ichiro、Fukui Norihito、Shinokubo Hiroshi
    • Journal Title

      Chemical Science

      Volume: 12 Issue: 14 Pages: 5224-5229

    • DOI

      10.1039/d1sc00438g

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Molecular motion of halogenated ethylammonium/[18]crown-6 supramolecular ions in nickel dithiolate magnetic crystals2021

    • Author(s)
      Hasuo Naohiro、Takahashi Kiyonori、Hisaki Ichiro、Kokado Kenta、Nakamura Takayoshi
    • Journal Title

      CrystEngComm

      Volume: in press Issue: 14 Pages: 2756-2763

    • DOI

      10.1039/d1ce00253h

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Triaxially Woven Hydrogen‐Bonded Chicken Wires of a Tetrakis(carboxybiphenyl)ethene2020

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

      Chemistry -A European Journal

      Volume: 26 Issue: 71 Pages: 17056-17062

    • DOI

      10.1002/chem.202002546

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] An Europium(III) Luminophore with Pressure‐Sensing Units: Effective Back Energy Transfer in Coordination Polymers with Hexadentate Porous Stable Networks2020

    • Author(s)
      Hasegawa Yasuchika、Sawanobori Takuya、Kitagawa Yuichi、Shoji Sunao、Fushimi Koji、Nakasaka Yuta、Masuda Takao、Hisaki Ichiro
    • Journal Title

      ChemPlusChem

      Volume: 85 Issue: 9 Pages: 1989-1993

    • DOI

      10.1002/cplu.202000513

    • NAID

      120007145355

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hydrogen-bonded organic frameworks of twisted polycyclic aromatic hydrocarbon2020

    • Author(s)
      Suzuki Yuto、Tohnai Norimitsu、Saeki Akinori、Hisaki Ichiro
    • Journal Title

      Chemical Communications

      Volume: 56 Issue: 87 Pages: 13369-13372

    • DOI

      10.1039/d0cc06081j

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] One-dimensional DABCO hydrogen-bonding chain in a hexagonal channel of magnetic [Ni(dmit)2]2020

    • Author(s)
      Li Simin、Takahashi Kiyonori、Hisaki Ichiro、Kokado Kenta、Nakamura Takayoshi
    • Journal Title

      Dalton Transactions

      Volume: 49 Issue: 46 Pages: 16772-16777

    • DOI

      10.1039/d0dt03386c

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Positional Effects of Annelated Pyrazine Rings on Structure and Stability of Hydrogen-Bonded Frameworks of Hexaazatrinaphthylene Derivatives2020

    • Author(s)
      Ichiro Hisaki, Qin Ji, Kiyonori Takahashi, Norimitsu Tohnai, Takayoshi Nakamura
    • Journal Title

      Cryst. Growth Des.

      Volume: 20 Issue: 5 Pages: 3190-3198

    • DOI

      10.1021/acs.cgd.0c00055

    • NAID

      120007034037

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Shape-Persistent Phenylene-Ethynylene Macrocycles Spectroscopy and Dynamics: From Molecules to the Hydrogen-Bonded Organic Framework Material2020

    • Author(s)
      Eduardo Gomez, Maria Rosaria di Nunzio, Miquel Moreno, Ichiro, Hisaki, Abderrazzak Douhal
    • Journal Title

      J. Phys. Chem. C

      Volume: 124 Issue: 12 Pages: 6938-6951

    • DOI

      10.1021/acs.jpcc.0c01369

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Hydrogen-Bonded Porous Frameworks Constructed by Rigid π-Conjugated Molecules with Carboxy Groups2020

    • Author(s)
      Ichiro Hisaki
    • Journal Title

      J. Incl. Phenom. Macro. Chem.

      Volume: 96 Issue: 3-4 Pages: 215-231

    • DOI

      10.1007/s10847-019-00972-0

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Spectroscopy and Dynamics of a HOF and Its Molecular Units: Remarkable Vapor Acid Sensing2019

    • Author(s)
      Eduardo Gomez, Yuto Suzuki, Ichiro Hisaki, Miquel Moreno, Abderrazzak Douhal
    • Journal Title

      J. Mater. Chem. C

      Volume: 7 Issue: 35 Pages: 10818-10832

    • DOI

      10.1039/c9tc03830b

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Template-Free Synthesis of a Phenanthroline-Containing [2]Rotaxane: A Reversible pH-Controllable Molecular Switch2019

    • Author(s)
      Masahiro Muraoka, Kakeru Aoyama, Sae Fujihara, Risa Yamane, Ichiro Hisaki, Mikiji Miyata, Michihisa Murata, Yohji Nakatsuji
    • Journal Title

      Symmetry

      Volume: 11 Issue: 9 Pages: 1137-1137

    • DOI

      10.3390/sym11091137

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Three-dimensional Aromaticity in an Antiaromatic Cyclophane2019

    • Author(s)
      Ryo Nozawa, Jinseok Kim, Juwon Oh, AnnaKamping, Yemei Wang, Soji Shimizu, Ichiro Hisaki, Tim Kowalczyk, Heike Fliegl, Dongho Kim, Horoshi Shinokubo
    • Journal Title

      Nat. Comm.

      Volume: 10 Issue: 1 Pages: 3576-3576

    • DOI

      10.1038/s41467-019-11467-4

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Acid Responsive Hydrogen-bonded Organic Framework2019

    • Author(s)
      Ichiro Hisaki, Yuto Suzuki, Eduardo Gomez, Qin Ji, Norimitsu Tohnai, Takayoshi Nakamura, Abderrazzak Douhal
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 141 Issue: 5 Pages: 2111-2121

    • DOI

      10.1021/jacs.8b12124

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Designing Hydrogen‐Bonded Organic Frameworks (HOFs) with Permanent Porosity2019

    • Author(s)
      Ichiro Hisaki, Chen Xin, Kiyonori Takahashi, Takayoshi Nakamura
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 58 Issue: 33 Pages: 11160-11170

    • DOI

      10.1002/anie.201902147

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] C3 Symmetric Hexaphenyltriphenylenehexamide: Molecular Design of Fluorescent Ferroelectrics2018

    • Author(s)
      Takashi Takeda, Jianyun Wu, Nobuaki Ikenaka, Norihisa Hoshino, Ichiro Hisaki, Tomoyuki Akutagawa
    • Journal Title

      ChemistrySelect

      Volume: 3 Issue: 38 Pages: 10608-10614

    • DOI

      10.1002/slct.201802317

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] CO2 Sorption of Layered Hydrogen-bonded Organic Framework Causes Reversible Structural Changes Involving Four Different Crystalline States under Ambient Pressure2018

    • Author(s)
      Ichiro Hisaki, Shoichi Nakagawa, Yuto Suzuki, Norimitsu Tohnai
    • Journal Title

      Chem. Lett.

      Volume: 47 Issue: 9 Pages: 1143-1146

    • DOI

      10.1246/cl.180491

    • NAID

      130007472114

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Docking Strategy to Construct Thermostable, Single-Crystalline, Hydrogen-Bonded Organic Framework with High Surface Area2018

    • Author(s)
      Hisaki, Ichiro; Suzuki, Yuto; Gomez, Eduardo; Cohen, Boiko; Tohnai, Norimitsu; Douhal, Abderrazzak
    • Journal Title

      Angewandte Chemie, International Edition

      Volume: 57 Issue: 39 Pages: 12650-12655

    • DOI

      10.1002/anie.201805472

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Single Crystal Fluorescence Behavior of a New HOF Material: Potential Candidate for a New LED2018

    • Author(s)
      Eduardo Gomez, Mario Gutierrez, Boiko Cohen, Ichiro Hisaki, Abderrazzak Douhal
    • Journal Title

      J. Mater. Chem. C

      Volume: 6 Issue: 26 Pages: 6929-6939

    • DOI

      10.1039/c8tc01808a

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] Porous Molecular Crystalline Materials Constructed through Intermolecular Hydrogen Bonds2021

    • Author(s)
      Ichiro Hisaki
    • Organizer
      Asian Conference on Crystal Growth and Crystal Technology
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] テトラフェニルエテン誘導体が形成する水結合性二次元ネットワークの編み込み集積構造とその蛍光挙動2021

    • Author(s)
      鈴木悠斗, 藤内謙光, 久木一朗
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Benefits of twisted conformation for developing porous organic frameworks2020

    • Author(s)
      Iciro Hisaki
    • Organizer
      Molecular Chirality Asia
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 水素結合で有機分子をつなげて組み立てた多孔質材料2020

    • Author(s)
      久木一朗
    • Organizer
      ゼオライトセミナー
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] π共役分子をかみ合いスタッキングで組み上げた大空孔水素結合性有機フレームワークの構築2020

    • Author(s)
      鈴木悠斗, 久木一朗, 藤内謙光
    • Organizer
      , 第30回基礎有機化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 水素結合を介したパイ共役分子の自己集合による有機多孔質構造体の構築2019

    • Author(s)
      久木一朗
    • Organizer
      第17回ホスト-ゲスト・超分子シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] Layered Organic Frameworks Constructed through Hydrogen-bonding2019

    • Author(s)
      I. Hisaki
    • Organizer
      Conference on the Chemistry of the Organic Solid State
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Hexaazatriphenylene- and Hexaazatrinaphtylene-based Porous Frameworks Constructed through Hydrogen-bonding2019

    • Author(s)
      I. Hisaki, Y. Suzuki, E. Gomez, Q. Ji, N. Tohnai,K. Takahashi, T. Nakamura, A. Douhal
    • Organizer
      The 18th International Symposium on Novel Aromatic Compounds
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ヘキサアザトリフェニレンのかみ合い積層による水素結合性多孔質構造体の構築とその限界2019

    • Author(s)
      久木一朗, 鈴木悠斗, G. Eduardo, 藤内謙光, A. Douhal
    • Organizer
      有機結晶シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] Hydrogen-bonded Porous Frameworks with pi-Conjugated Systems2019

    • Author(s)
      I. Hisaki
    • Organizer
      π-EJ 2019 (pi-System Figuration European-Japanese Workshop 2019)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Hydrogen-bonded Organic Frameworks2019

    • Author(s)
      I. Hisaki
    • Organizer
      2019 International Symposium of Research Institute for Electronic Science (RIES) and Center for Emerging Functional Matter Science (CEFMS)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 水素結合により組み立てる永続的多孔性フレームワーク2019

    • Author(s)
      久木一朗
    • Organizer
      東京工業大学 化学生命科学研究所 講演会「超分子化学-その未来-」
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Acid-responsive Porous Hydrogen-bonded Organic Framework2019

    • Author(s)
      Ichiro Hisaki, Yuto Suzuki, Eduardo Gomez, Qin Ji, Norimitsu Tohnai, Takayoshi Nakamura, Abderrazzak Douhal
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 水素結合性多孔質フレームワーク2018

    • Author(s)
      久木一朗
    • Organizer
      第7回錯体化学若手の会北海道支部勉強会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 水素結合性多孔質フレームワーク~パイ共役系を高次超分子シントンで組み上げる~2018

    • Author(s)
      久木一朗
    • Organizer
      第12回超分子若手懇談会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Hexaazatriphenylene-based, Thermally Stable, Single Crystalline HOF with Permanent Porosity2018

    • Author(s)
      Ichiro Hisaki, Nobuaki Ikenaka, Yuto Suzuki, Eduardo Gomez, Boiko Cohen, Norimitsu Tohnai, Abderrazzak Douhal
    • Organizer
      13th International Workshop of the Crystal Growth of Organic Material
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ヘキサアザトリナフチレン誘導体の水素結合性多孔質フレームワーク2018

    • Author(s)
      久木一朗, 鈴木悠斗, Eduardo Gomez, 藤内謙光, 中村貴義, Abderrazzak Douhal
    • Organizer
      第27回有機結晶シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] 水素結合性ヘキサゴナルネットワークの積層による機能性多孔質構造の構築2018

    • Author(s)
      久木一朗
    • Organizer
      高分子討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 酸の刺激で呈色する水素結合性有機フレームワーク2018

    • Author(s)
      久木一朗, 鈴木悠斗, 藤内謙光
    • Organizer
      基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] C3対称性のヘキサアザトリナフチレン誘導体を基盤とした水素結合性多孔質フレームワーク:構造とその物性2018

    • Author(s)
      久木一朗, 鈴木悠斗, 藤内謙光
    • Organizer
      第64回高分子研究発表会 神戸
    • Related Report
      2018 Annual Research Report
  • [Book] Advances in Organic Crystal Chemistry2020

    • Author(s)
      Ichiro Hisaki, Qin Ji, Kiyonori Takahashi, Takayoshi Nakamura
    • Total Pages
      21
    • Publisher
      Springer
    • Related Report
      2020 Annual Research Report
  • [Remarks] 大阪大学大学院基礎工学研究科物質創成専攻機能物質化学領域分子集積化学グループHP

    • URL

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

    • Related Report
      2020 Annual Research Report
  • [Remarks] 大阪大学大学院基礎工学研究科物質創成専攻久木研究室

    • URL

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

    • Related Report
      2019 Annual Research Report
  • [Remarks] 所属研究室HP

    • URL

      http://fnm.es.hokudai.ac.jp/

    • Related Report
      2018 Annual Research Report
  • [Remarks] 研究者HP

    • URL

      http://fnm.es.hokudai.ac.jp/members/hisaki/home_J.html

    • Related Report
      2018 Annual Research Report

URL: 

Published: 2018-04-23   Modified: 2022-01-27  

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