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2013 Fiscal Year Final Research Report

Ring-Fused Malonamides as a Novel Hydrogen-bonding Motif: Construction of Supramolecular Architectures with Controlled Dimensionality

Research Project

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Project/Area Number 23655024
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, 准教授 (50322798)

Co-Investigator(Kenkyū-buntansha) SUZUKI Takanori  北海道大学, 大学院・理学研究院, 教授 (70202132)
Project Period (FY) 2011 – 2013
Keywords水素結合 / アミド / 結晶構造 / 次元制御 / 自己集合 / 超分子 / ナノチューブ / ゲル
Research Abstract

Ring-fused malonamides with two primary amide groups, such as 2,2-indanedicarboxamides, assemble into well-defined 2D-sheet structures based on the formation of 6 to 8 hydrogen bonds per molecule. The fused ring part would be planted above and below the 2D-sheet by supporting with multiple hydrogen-bondings. The stacking manner and the interlayer distances of these sheets in crystal can be manipulated by varying the size of the fused ring, to form either interdigitated or segregated structures. Furthermore, triptycene-fused malonamides for the purpose of formation to tubular structures by rolling 2D-sheet into a cylinder due to their steric hindrance of triptycenes. We revealed their hydrogen-bonding patterns to assemble a tubluar structure by powder X-ray structural analysis. This motif technique allows the ready design of crystalline materials wherein the various functionalities are situated in well-ordered arrays.

  • Research Products

    (11 results)

All 2013 2012 2011

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (6 results)

  • [Journal Article] Geometrical Remote Steric Effects in 4, 5-Disubstituted-9, 10-dihydrophenanthrene s : Expansion of Prestrained C9-C10 Bond in Di(spiroacridan) Derivatives2013

    • Author(s)
      K. Wada, T. Takeda, H. Kawai, R. Katoono, K. Fujiwara, T. Suzuki
    • Journal Title

      Chem. Lett

      Volume: vol. 42 Pages: 1194-1196

    • DOI

      10.1246/cl.130502

    • Peer Reviewed
  • [Journal Article] Hexaphenylethanes with an ultralong C-C bond : Expandability of the C-C bond in highly strained tetraarylpyracenes2013

    • Author(s)
      T. Takeda, Y. Uchimura, H. Kawai, R. Katoono, K. Fujiwara, T. Suzuki
    • Journal Title

      Chem. Lett

      Volume: vol. 42 Pages: 954-962

    • DOI

      10.1246/cl.130598

    • Peer Reviewed
  • [Journal Article] Stable Neutral Radicals Based on the Polyazaacene Skeleton that Exhibit High Electrochemical Amphotericity2012

    • Author(s)
      M. Miura, H. Chiba, R. Katoono, H. Kawai, K. Fujiwara, S. Suzuki, K. Okada, T. Suzuki
    • Journal Title

      Tetrahedron Lett

      Volume: vol. 53 Pages: 6561-6562

    • DOI

      10.1016/j.tetlet.2012.09.095

    • Peer Reviewed
  • [Journal Article] Assembly of Robust Two Dimensional Sheet Structures from Crystalline Ring-Fused Malonamides via Cooperative Hydrogen Bonding of Amide Groups2012

    • Author(s)
      H. Kawai, D. Hosoda
    • Journal Title

      Cryst Eng Comm

      Volume: vol. 14 Pages: 5717-5719

    • DOI

      10.1039/C2CE26003D

    • Peer Reviewed
  • [Journal Article] Molecular Gyroscope with a trans-Cyclohexane-1, 4-diimine Rotor Unit : Isolation and Characterization of a Geometric Isomer as a Formal Intermediate of Hindered Rotation2012

    • Author(s)
      H. Sugino, H. Kawai, K. Fujiwara, T. Suzuki
    • Journal Title

      Chem. Lett

      Volume: vol. 41 Pages: 79-81

    • DOI

      10.1246/cl.2012.79

    • Peer Reviewed
  • [Presentation] インダンジカルボキサミドに基づくシート構造およびチューブ構造の構築とその結晶構造2013

    • Author(s)
      河合英敏
    • Organizer
      第22回有機結晶シンポジウム
    • Place of Presentation
      札幌
    • Year and Date
      2013-10-31
  • [Presentation] トリプチセン縮環マロナミドが形成するチューブ状構造 : X線構造解析により明らかになった水素結合様式2013

    • Author(s)
      高田知伸, 河合英敏
    • Organizer
      第24回基礎有機化学討論
    • Place of Presentation
      東京都豊島区
    • Year and Date
      2013-09-05
  • [Presentation] トリプチセン縮環マロナミドの水素結合ネットワーク形成による1次元伸長構造への自己集合2013

    • Author(s)
      高田知伸, 河合英敏
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津
    • Year and Date
      2013-03-23
  • [Presentation] アミド基の協同性を利用した超分子および次元制御構造の構築2012

    • Author(s)
      河合英敏
    • Organizer
      2012高分子・ハイブリッド材料研究センター(PHyM)若手フォーラム
    • Place of Presentation
      仙台
    • Year and Date
      2012-12-21
  • [Presentation] 縮環マロナミドを水素結合モチーフとする次元制御構造の構築2012

    • Author(s)
      河合英敏
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都
    • Year and Date
      2012-09-21
  • [Presentation] インダンジカルボキサミドを水素結合モチーフとする次元制御構造の構築2011

    • Author(s)
      河合英敏
    • Organizer
      第72回応用物理学会学術講演会
    • Place of Presentation
      山形
    • Year and Date
      2011-08-30

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Published: 2015-06-25  

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