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Creation of Hydrogen Storage Material Based on Cooperative Effects of Accumulated Acetylenes with Well-defined Geometry

Research Project

Project/Area Number 24685026
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypePartial Multi-year Fund
Research Field Functional materials chemistry
Research InstitutionOsaka University

Principal Investigator

HISAKI Ichiro  大阪大学, 工学(系)研究科(研究院), 助教 (90419466)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥26,650,000 (Direct Cost: ¥20,500,000、Indirect Cost: ¥6,150,000)
Fiscal Year 2014: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2013: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2012: ¥18,460,000 (Direct Cost: ¥14,200,000、Indirect Cost: ¥4,260,000)
Keywords超分子化学 / 結晶工学 / 多孔質材料 / ガス吸着 / 水素結合 / デヒドロアヌレン / ヘキサゴナルネットワーク / 集積アセチレン / 多孔性材料 / 配位ポリマー / 金属‐有機構造体 / パイ共役分子 / アヌレン / 水素吸蔵 / 金属-有機フレームワーク / アセチレン / デヒドロベンゾアヌレン
Outline of Final Research Achievements

Porous materials composed of acetylenes, highly-unsaturated sterically-narrow chemical species, are expected to absorb hydrogen gas molecules physically and chemically. In this study, we aimed construction of such materials based on pi-conjugated macrocyclic molecules so-called dehydrobenzoannulene (DBA), possessing acetylene moieties preorganized with well-defined geometry. First, we elucidate quantitative intermolecular interactions between the DBA and gas molecules. Subsequently, we successfully constructed porous materials, in which DBA molecules are networked via coordination bonds or hydrogen bonds to form nano-meter pores surrounded by DBA. Some of them show good gas absorption property.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • Research Products

    (39 results)

All 2015 2014 2013 2012 Other

All Journal Article (12 results) (of which Peer Reviewed: 12 results,  Acknowledgement Compliant: 4 results,  Open Access: 3 results) Presentation (26 results) (of which Invited: 3 results) Book (1 results)

  • [Journal Article] Synthesis of Chiral Assembly from Achiral Octadehydrotribenzo[14]annulene Derivative by Using Twofold Helical Hydrogen Bonding Template2015

    • Author(s)
      1.Ichiro Hisaki, Eriko Kometani, Hajime Shigemitsu, Norimitsu Tohnai, Mikiji Miyata
    • Journal Title

      Synlett

      Volume: 印刷中

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] C3-Symmetric Macrocycle-Based, Hydrogen-Bonded, Multi-Porous Hexagonal Network as Motif of Porous Molecular Crystals2015

    • Author(s)
      2.Ichiro Hisaki, Shoichi Nakagawa, Norimitsu Tohnai, Mikiji Miyata
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 15 Issue: 10 Pages: 3008-3012

    • DOI

      10.1002/anie.201411438

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] One-Step Reaction that Yields Highly Twisted and Fully π-Conjugated Porphyrinic Oligomers2015

    • Author(s)
      Satoru Ito, Satoru Hiroto, Sangsu Lee, Minjung Son, Ichiro Hisaki, Takuya Yoshida, Dongho Kim, Nagao Kobayashi, Hiroshi Shinokubo
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 137 Issue: 1 Pages: 142-145

    • DOI

      10.1021/ja511905f

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Crystal Structure of Hydrogen-Bond Assisted Coaxially pi-Stacked Dimer of Hexadehydrotribenzo[12]annulene ([12]DBA) Derivative2014

    • Author(s)
      Ichiro Hisaki, Keisuke Osaka, Hajime Shigemitsu, Norimitsu Tohnai, Mikiji Miyata
    • Journal Title

      Chem. Lett.

      Volume: 43 Issue: 7 Pages: 11041106-11041106

    • DOI

      10.1246/cl.140250

    • NAID

      130004868257

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Effects of ortho-Phenyl Substitution on Molecular Arrangements of Octadehydrodibenzo[12]annulene2014

    • Author(s)
      Ichiro Hisaki, Noriko Manabe, Keisuke Osaka, Akinori Saeki, Shu Seki, Norimitsu Tohnai, Mikiji Miyata
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 87 Pages: 323-333

    • NAID

      40019978498

    • Related Report
      2014 Annual Research Report 2013 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Crystal Structure of Hydrogen-Bond Assisted Coaxially pi-Stacked Dimer of Hexadehydrotribenzo[12]annulene ([12]DBA) Derivative2014

    • Author(s)
      Ichiro Hisaki, Keisuke Osaka, Hajime Shigemitsu, Norimitsu Tohnai, Mikiji Miyata
    • Journal Title

      Chem. Lett.

      Volume: just accepted

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Highly Crystalline Supramolecular Nanofibers Based on Dehydrobenzoannulene Derivatives2013

    • Author(s)
      Hajime Shigemitsu, Ichiro Hisaki, Eriko Kometani, Daisuke Yasumiy a, Yuu Sakamoto, Keisuke Osaka, Tejender S. Thakur, Akinori Saeki, Shu Seki, Fumiko Kimura, Tsunehisa Kimura, Norimitsu Tohnai, Mikiji Miyata
    • Journal Title

      Chemist a European Journal

      Volume: 19 Issue: 45 Pages: 15366-15377

    • DOI

      10.1002/chem.201301967

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Structural Transformation between the Supramolecular Nanofibers with Dr2stic Change of Conductivity by Heat and Ultrasound2013

    • Author(s)
      Hajime Shigemitsu, Ichiro Hisaki, Hirofumi Senga, Daisuke Yasumiya, Tejender S. Thakur, Akinori Saeki, Shu Seki, Norimitsu Tohnai, Mikiji Miyata
    • Journal Title

      Chemistry An Asian Journal

      Volume: 未定(掲載確定) Issue: 7 Pages: 1372-1376

    • DOI

      10.1002/asia.201300258

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Boron-Containing PAH as a Substructure of Boron-Doped Graphene2012

    • Author(s)
      Chuandong Dou, 他
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 51 Issue: 49 Pages: 12206-12210

    • DOI

      10.1002/anie.201206699

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Interactions Between Dehydrobenzo [12] annulene (DBA) and Gas Molecules: Do the Preorganized Acetylenes Work Cooperatively?2012

    • Author(s)
      Ichiro Hisaki, Daisuke Yasumiya, Hajime Shigemitsu, Seiji Tsuzuki, Norimitsu Tohnai, Mikiji Miyata
    • Journal Title

      Physical Chemistry Chemical Physics

      Volume: 14 Issue: 40 Pages: 13918-13921

    • DOI

      10.1039/c2cp43091f

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Crystal Structure of Quinine : Unignorable Affects of Vinyl and Methoxy Groups on Molecular Assemblies of Cinchona Alkaloids2012

    • Author(s)
      Ichiro Hisaki, Eri Hiraishi, Toshiyuki Sasaki, Hideo Orita, Seiji Tsuzuki, Norimitsu Tohnai, and Mikiji Miyata
    • Journal Title

      Chem. Asian J

      Volume: 7 Issue: 11 Pages: 2607-2614

    • DOI

      10.1002/asia.201200566

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Guest-Dependent Structural Transformation of Dehydrobenzoannulene Inclusion Crystals Composed of π-Stacked Parallelogram Columnar Motifs2012

    • Author(s)
      Hajime Shigemitsu, Ichiro Hisaki, Eriko Kometani, Norimitsu Tohnai, Mikiji Miyata
    • Journal Title

      Chemistry Letters

      Volume: 41 Issue: 11 Pages: 1535-1537

    • DOI

      10.1246/cl.2012.1535

    • NAID

      10031126590

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Presentation] Hydrogen-Bonded Multiporous Hexagonal Networks Composed of C3-Symmetric pi-Conjugated Macrocycles2015

    • Author(s)
      Ichiro Hisaki, Shoichi Nakagawa, Nobuaki Ikenaka, Norimitsu Tohnai, Mikiji Miata
    • Organizer
      22nd International Conference on the Chemistry of the Organic Solid State (ICCOSS)
    • Place of Presentation
      TOKI MESSE, 新潟
    • Year and Date
      2015-07-12 – 2015-07-17
    • Related Report
      2014 Annual Research Report
  • [Presentation] Ichiro Hisaki, Shoichi Nakagawa, Nobuaki Ikenaka, Norimitsu Tohnai, Mikiji Miyata2015

    • Author(s)
      Triangular Aromatics-Based, Hydrogen-Bonded, Multiporous
    • Organizer
      16th International Symposium on Novel Aromatic Compound (ISNA)
    • Place of Presentation
      Madrid, Spain
    • Year and Date
      2015-07-05 – 2015-07-10
    • Related Report
      2014 Annual Research Report
  • [Presentation] Structure and Property of pi-Stacked Assembly of Thienyl-Substituted Octadehydro[12]annulene2015

    • Author(s)
      Ichiro Hisaki, Keisuke Osaka, Norimitsu Tohnai, Mikiji Miyata
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学船橋キャンパス、千葉
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] デヒドロベンゾ[18]アヌレンを基盤とした水素結合性低密度ヘキサゴナルネットワークの構造とその動的物性2015

    • Author(s)
      中川祥一、久木一朗、藤内謙光、宮田幹二
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学船橋キャンパス、千葉
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] Structure and Dynamic Behavior of Laminated Porous Hexagonal Networks Composed of Triphenylene Hexacarboxylic Acid Derivative2015

    • Author(s)
      Nomuaki Ikenaka, Ichiro Hisaki, Norimitsu Tohnai, Mikiji Miyata
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学船橋キャンパス、千葉
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] Twofold Helical Molecular Assembly in Organic Crystal2014

    • Author(s)
      Ichiro Hisaki, Toshiyuki Sasaki, Norimitsu Tohnai, Mikiji Miyata
    • Organizer
      Molecular Chirality Asia 2014
    • Place of Presentation
      Beijing, China
    • Year and Date
      2014-10-29 – 2014-10-31
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] C3対称性パイ共役環状分子を基盤とした結晶性超分子構造体の構築と機能2014

    • Author(s)
      久木一朗
    • Organizer
      有機結晶シンポジウム
    • Place of Presentation
      東邦大学習志野キャンパス、千葉
    • Year and Date
      2014-10-15 – 2014-10-17
    • Related Report
      2014 Annual Research Report
  • [Presentation] パイ共役環状分子を基盤とした水素結合性低密度ヘキサゴナルネットワークの構築2014

    • Author(s)
      久木一朗, 中川祥一, 藤内謙光, 宮田幹二
    • Organizer
      第63回高分子討論会
    • Place of Presentation
      長崎大学文教キャンパス、長崎
    • Year and Date
      2014-09-24 – 2014-09-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] Affirmative Polymorph Generation of Annulenes by Using CH/O Interactions2014

    • Author(s)
      Ichiro Hisaki, Norimitsu Tohnai, Mikiji Miyata
    • Organizer
      IUCr2014
    • Place of Presentation
      Montreal, Canada
    • Year and Date
      2014-08-05 – 2014-08-12
    • Related Report
      2014 Annual Research Report
  • [Presentation] Metal Coordinated Supramolecular Architectures Based on Dehydrobenzoannulenes2014

    • Author(s)
      Ichiro Hisaki, Norimitsu Tohnai, Mikiji Miyata
    • Organizer
      International Conference on Organometallic Chemistry 2014 (ICOMC)
    • Place of Presentation
      Royton Sapporo、北海道
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] Affirmative Generation of Dehydrobenzoannulene Polymorphs2014

    • Author(s)
      Ichiro Hisaki, Norimitsu Tohnai, Mikiji Miyata
    • Organizer
      Joint Congres of ACTS-2014 and CGOM11
    • Place of Presentation
      Nara Prefectural New Public Hall、 奈良
    • Year and Date
      2014-06-17 – 2014-06-20
    • Related Report
      2014 Annual Research Report
  • [Presentation] Crystalline Supramolecular Nanofibers Based on Dehydrobenzoannulene Derivatives2014

    • Author(s)
      Ichiro Hisaki
    • Organizer
      94th Annual Meeting of The Chemical Society of Japan
    • Place of Presentation
      Nagoya
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] メチルエステル置換した非中心対称性アヌレンによる結晶性ナノファイバーの構築2013

    • Author(s)
      久木一朗
    • Organizer
      第60回応用物理学会春季学術講演会
    • Place of Presentation
      神奈川
    • Year and Date
      2013-03-29
    • Related Report
      2012 Annual Research Report
  • [Presentation] 超音波による高結晶性超分子ナノファイバーの動的構造変換および電気的特性変化2013

    • Author(s)
      重光孟, 他
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀
    • Year and Date
      2013-03-24
    • Related Report
      2012 Annual Research Report
  • [Presentation] アリール置換によるオクタデヒドロ[12]アヌレンの積層構造制御2013

    • Author(s)
      久木一朗
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀
    • Year and Date
      2013-03-23
    • Related Report
      2012 Annual Research Report
  • [Presentation] Solid-State Supramolecular Assemblies Based on Dehydrobenzoannulene2013

    • Author(s)
      Ichiro Hisaki
    • Organizer
      China-Japan Joint Symposium on Functional Supramolecular Architectures
    • Place of Presentation
      Suzhou, China
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] ひずみ環状ブタジインの積層構造制御2013

    • Author(s)
      久木 一朗
    • Organizer
      第62回高分子学会年次大会
    • Place of Presentation
      京都
    • Related Report
      2013 Annual Research Report
  • [Presentation] アセチレンを集積した環状分子による多孔性配位ポリマーの構築2013

    • Author(s)
      安宮大祐
    • Organizer
      第62回高分子学会年次大会
    • Place of Presentation
      京都
    • Related Report
      2013 Annual Research Report
  • [Presentation] Highly Crystalline Supramolecular Nanofibers based on Dehvdrobenzoannulenes and their Ultrasound Resoonsivity2012

    • Author(s)
      Hajime Shigemitsu, 他
    • Organizer
      Japan-Taiwan Bilateral Workshop on Nano-Science 2012
    • Place of Presentation
      大阪
    • Year and Date
      2012-12-05
    • Related Report
      2012 Annual Research Report
  • [Presentation] Construction of One-Dimensionally π-Stacked Assemblies with Inclusion Channels Using Triangular Dehydrobenzoannulenes2012

    • Author(s)
      Hajime Shigemitsu, 他
    • Organizer
      The Twelfth International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-12)
    • Place of Presentation
      京都
    • Year and Date
      2012-11-13
    • Related Report
      2012 Annual Research Report
  • [Presentation] アセチレンを明確な幾何配置に固定した環状共役分子の気体分子に対する親和性2012

    • Author(s)
      久木一朗
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都
    • Year and Date
      2012-09-21
    • Related Report
      2012 Annual Research Report
  • [Presentation] Porous Crystalline Architectures Based on Triangular Dehydrobenzoannulene Derivatives2012

    • Author(s)
      久木一朗
    • Organizer
      Gordon Research Conference on Crystal Engineering
    • Place of Presentation
      NH USA
    • Year and Date
      2012-06-11
    • Related Report
      2012 Annual Research Report
  • [Presentation] Construct ion of One-Dimensionally π-Stacked Assemblies with Inclusion Channels via Symmetry Decreasing Crystallization of C3 Discotic Molecules2012

    • Author(s)
      久木一朗
    • Organizer
      61st SPSJ Annual Meeting
    • Place of Presentation
      神奈川
    • Year and Date
      2012-05-31
    • Related Report
      2012 Annual Research Report
  • [Presentation] Highly crystalline one-dimensional supramolecular assemblies based on oolar dehvdrobenzoannulene derivatives2012

    • Author(s)
      Hajime Shigemitsu, 他
    • Organizer
      第61回高分子学会年次大会
    • Place of Presentation
      横浜
    • Year and Date
      2012-05-31
    • Related Report
      2012 Annual Research Report
  • [Presentation] Highly crystalline one-dimensional supramolecular assemblies based on polar dehvdrobenzoannulene derivatives2012

    • Author(s)
      Hajime Shigemitsu, 他
    • Organizer
      14th International Associat ion of Colloid and Interface
    • Place of Presentation
      仙台
    • Year and Date
      2012-05-16
    • Related Report
      2012 Annual Research Report
  • [Presentation] メチルエステル基をもつ非中心対称性デヒドロベンゾアヌレン(DBA)の結晶性超分子ナノファイバーの構築と物性

    • Author(s)
      久木一朗
    • Organizer
      基礎有機化学討論会
    • Place of Presentation
      東京
    • Related Report
      2013 Annual Research Report
  • [Book] ゲルの安定化と機能性付与・次世代への応用開発2013

    • Author(s)
      久木一朗、藤内謙光、宮田幹二
    • Total Pages
      552
    • Publisher
      技術情報協会
    • Related Report
      2013 Annual Research Report

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Published: 2012-04-24   Modified: 2019-07-29  

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