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Construction of Dimensional-controlled Structures based on Conformational Chirality Control in Ring-fused Malonamides

Research Project

Project/Area Number 26620035
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionTokyo University of Science

Principal Investigator

Kawai Hidetoshi  東京理科大学, 理学部第一部化学科, 准教授 (50322798)

Research Collaborator FUKUSHIMA Takanori  東京工業大学, 化学生命科学研究所, 教授 (70281970)
TADOKORO Makoto  東京理科大学, 理学部第一部化学科, 教授 (60249951)
ONO Kosuke  東京理科大学, 理学部第一部化学科, 助教 (30579313)
Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2016: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2015: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywords水素結合 / クリスタルエンジニアリング / アミド / X線構造解析 / キラル空間 / らせん / 多孔質構造 / ナノチューブ / 多孔質材料 / キラル / 多孔性結晶 / 配座キラリティー / 螺旋構造 / ビナフチル
Outline of Final Research Achievements

We have found that 2,2-indandicarboxamides assembled into the robust 2D-sheet structures based on formation of eight hydrogen bonds per molecule in the solid state. These sheet structures densely stack on one another in an interdigitated manner, therefore, any cavities, in which guests could be included, were formed among these sheets. In this work, we prepared chiral ring-fused malonamides, such as binaphthalene-fused malonamides, to create inclusion crystals with chiral inclusion cavities among these sheets by biasing the conformational chirality of the malonamide moiety toward either one, and by regulating possible hydrogen-bonding patterns. We found that the substituents at the 3,3’-position of the binaphthalene moiety effect on the conformational chirality of malonamide moiety and change the assembling dimensionality from 2D-sheet to 1D-helical structures. Furthermore, we also prepared pi-bridged bis(malonamide)s to construct hydrogen-bonded pillared-layer porous frameworks.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (9 results)

All 2016 2015 2014

All Journal Article (1 results) (of which Peer Reviewed: 1 results,  Open Access: 1 results,  Acknowledgement Compliant: 1 results) Presentation (8 results) (of which Int'l Joint Research: 1 results,  Invited: 1 results)

  • [Journal Article] Hydrindacenes as Versatile Supramolecular Scaffolds2015

    • Author(s)
      Hidetoshi Kawai
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 88 Issue: 3 Pages: 399-409

    • DOI

      10.1246/bcsj.20140313

    • NAID

      130004801838

    • ISSN
      0009-2673, 1348-0634
    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] ビナフチル縮環マロナミド類の配座キラリティー制御に基づく次元制御構造の構築2016

    • Author(s)
      清水貴広・古田えりか・小野公輔・河合英敏
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島市・広島国際会議場
    • Year and Date
      2016-09-02
    • Related Report
      2016 Annual Research Report
  • [Presentation] π架橋ビスマロナミドを用いた強固な水素結合性ピラードレイヤー型格子構造の構築とそのゲスト吸脱着能2016

    • Author(s)
      西城圭・斉藤勇人・小野公輔・田所誠・河合英敏
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京都市)
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
  • [Presentation] ビナフチル縮環マロナミド類のアミド配座キラリティー制御に基づく包接結晶の設計2016

    • Author(s)
      清水貴広・古田えりか・小野公輔・福島孝典・河合英敏
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京都市)
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
  • [Presentation] Conformational Chirality in the Hydrogen-bonded Assembly of Chiral Ring-fused Malonamides2015

    • Author(s)
      Takahiro Shimizu, Kosuke Ono, Takanori Fukushima, Hidetoshi Kawai
    • Organizer
      14th Symposium on Chemical Approaches to Chirality
    • Place of Presentation
      Morito Memorial Hall (Shinjuku-ku, Tokyo)
    • Year and Date
      2015-11-18
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] キラルな縮環構造を有する縮環マロナミドの配座キラリティー及び集合特性2015

    • Author(s)
      清水貴広・ 古田えりか・小野公輔・福島孝典・河合英敏
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛大学(愛媛県松山市)
    • Year and Date
      2015-09-25
    • Related Report
      2015 Research-status Report
  • [Presentation] アロステリックレセプターの開発とその応用を目指して2015

    • Author(s)
      河合英敏
    • Organizer
      第6回サブウェイセミナー
    • Place of Presentation
      中央大学(東京都文京区)
    • Year and Date
      2015-08-29
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] 新しい水素結合モチーフとしての縮環マロナミド:嵩高い骨格の導入によるチューブ構造への集積2014

    • Author(s)
      清水貴広・髙田知伸・福島孝典・河合英敏
    • Organizer
      第15回リング・チューブ超分子研究会シンポジウム
    • Place of Presentation
      東京都目黒区
    • Year and Date
      2014-10-27
    • Related Report
      2014 Research-status Report
  • [Presentation] 縮環マロナミド部を両端に有するπ拡張分子を用いた3次元格子構造の構築2014

    • Author(s)
      西城圭・斎藤勇人・立谷尚人・田所誠・河合英敏
    • Organizer
      第4回CSJ化学フェスタ
    • Place of Presentation
      東京都江東区
    • Year and Date
      2014-10-16
    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2018-03-22  

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