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新規超分子モチーフとしてのヒドリンダセン分子の特性研究

Research Project

Project/Area Number 16750024
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionHokkaido University

Principal Investigator

河合 英敏  北海道大学, 大学院・理学研究科, 助手 (50322798)

Project Period (FY) 2004 – 2005
Project Status Completed (Fiscal Year 2005)
Budget Amount *help
¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2005: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2004: ¥2,600,000 (Direct Cost: ¥2,600,000)
Keywords超分子 / 自己集合 / 分子認識 / アロステリック / マクロサイクル / イミン / 動的共有結合 / ロタキサン / 酸化還元 / 蛍光色素
Research Abstract

1)ヒドリンダセンジアミド誘導体のアロステリック会合に基づく超分子ポリマーの構築
正のホモトロピックなアロステリック会合能を有するヒドリンダセンジアミド体と、相補的な水素結合パートナーとなるレゾルシノールを連結したモノマーユニットを用いる核形成・伸張プロセスに基づく超分子ポリマー構築を目的とし、検討を行った。レゾルシノール部を片側にのみ持つモノマーを合成し、自己会合能を調査したところ、望みの自己会合様式に基づく2量化が認められた。また、この2量体へのアドレナリン添加においてアロステリック会合能およびそれに伴う2量体の解離が認められた。
2)光学活性ヒドリンダセンジアミド誘導体によるアドレナリン類の分子認識
先に開発したアドレナリン認識能を有するヒドリンダセンジアミド誘導体に、より高い分子認識能を付与すべく、光学活性アミノ酸の導入を行った。(E)-L-アラニン誘導体のアドレナリン認識能を調査したところ、会合強度の向上とともにジアステレオマー錯体を形成することがわかった。
3)ヒドリンダセンを軸分子とするイミン架橋型ロタキサンの構築とその特性
軸分子と環状分子とが可逆なイミン結合によって連結された動的共有結合連結型ロタキサンを開発した。この分子はイミン結合時には環が固定され、加水分解により環に自由度が付与される新規ロタキサン分子である。今年度はより柔軟な環部をもつ誘導体を合成し、その加水分解に基づく動的平衡を調査したところビスイミン体、モノイミン体および[2]ロタキサン間の平衡状態となることが確かめられた。さらにより低温で[2]ロタキサンの組成比が増加する興味深い現象が認められた。これはロタキサン構成要素間の運動性がより低温で増加していることを意味しており、新たな分子運動性の制御機構として応用が期待される。また、このもののチオアセタール化による非平衡な[2]ロタキサンへの変換にも成功した。

Report

(2 results)
  • 2005 Annual Research Report
  • 2004 Annual Research Report
  • Research Products

    (17 results)

All 2006 2005 2004

All Journal Article (17 results)

  • [Journal Article] Change in conformation upon complexation of double-armed terephthalamide hosts : dynamic molecular recognition of ditopic guests with strong CD signaling2006

    • Author(s)
      R.Katoono
    • Journal Title

      Tetrahedron Letters 47・10

      Pages: 1513-1516

    • Related Report
      2005 Annual Research Report
  • [Journal Article] The first stable tetraarylacenaphthenequinodimethanes exhibiting electrochromism with 'write-protect' option : Preparation, highly deformed structure, and reversible interconversion with acenaphthylene-5,6-diyl dicationic dyes2006

    • Author(s)
      T.Suzuki
    • Journal Title

      Tetrahedron Letters 47・4

      Pages: 467-471

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Stereospecific change in conformation upon complexation of an exoditopic tetraamide host with a bis(ammonium) guest : chiral recognition and strong CD signaling2005

    • Author(s)
      R.Katoono
    • Journal Title

      Chemical Communications -・41

      Pages: 5154-5156

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Isolation and low-temperature X-ray analysis of intramolecular triarylmethane-triarylmethylium complex : Preference of C-H bridged unsymmetric structure exhibiting facile 1,5-hydride shift and charge-transfer interaction2005

    • Author(s)
      H.Kawai
    • Journal Title

      Journal of the American Chemical Society 127・35

      Pages: 12172-12173

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Butane-1,4-diyl dications stabilized by steric factors : Electrochiroptical response systems based on reversible interconversion between dihydro[5]helicene-type electron acceptors and electron-donating 1,1'-binaphtyls2005

    • Author(s)
      E.Ohta
    • Journal Title

      Organic & Biomolecular Chemistry 3・16

      Pages: 3024-3031

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Exceptionally large difference in bond length among conformational isomorphs of a hexaphenylethane derivative with a dispiropyracene skeleton2005

    • Author(s)
      H.Kawai
    • Journal Title

      Crystal Growth & Design 5・6

      Pages: 2256-2260

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Tetracyanoanthraquinodimethanes with a chiral amide group : Preparation, properties, and charge-transfer photochirogenetic reaction with 1,2-dianisylacenaphthene-1,2-diol2005

    • Author(s)
      T.Suzuki
    • Journal Title

      Journal of Organic Chemistry 70・14

      Pages: 5592-5598

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Multipoint Recognition of Catecholamines by Hydrindacene-Based Receptors Accompanied by the Complexation-Induced Conformational Switching2005

    • Author(s)
      H.Kawai
    • Journal Title

      Chemistry, A European Journal 11・3

      Pages: 81-824

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Dynamic Redox Systems Based on Bis(spiroxanthene)-Type Donors with a Polycyclic Aromatic Hydrocarbon : Preparation, X-ray Structures and Electrochromic Response with Fluorescence Change2004

    • Author(s)
      T.Suzuki
    • Journal Title

      Tetrahedron Letters 45・46

      Pages: 8563-8567

    • Related Report
      2004 Annual Research Report
  • [Journal Article] [10]Paracyclophanediamides and Their Octadehydro Derivatives : Novel Exotopic Receptors with Hydrogen-Bonding Sites on the Bridge2004

    • Author(s)
      R.Katoono
    • Journal Title

      Tetrahedron Letters 45・46

      Pages: 8455-8459

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Short Nonbond and Long C-C Bond in Naphthalene-1,8-diylbis(10-methyl acridinium) and the Corresponding Hexaphenylethane Derivative : A New Electrochromic Pair Exhibiting Dynamic Reds Properties2004

    • Author(s)
      H.Kawai
    • Journal Title

      Tetrahedron Letters 45・45

      Pages: 8289-8293

    • Related Report
      2004 Annual Research Report
  • [Journal Article] First Stable 7,7,8,8-Tetraaryl-o-quinodimethane : Isolation, X-ray Structure, Electrochromic Response of 9,10-Bis(dianisylmethylene)-9,10-dihydrophenanthrene2004

    • Author(s)
      S.Iwashita
    • Journal Title

      Chemical Communications -・18

      Pages: 2076-2077

    • Related Report
      2004 Annual Research Report
  • [Journal Article] peri-Interaction between Diarylmethyl and Diarylmethylium Units in 1,8-Disubstituted Naphthalenes : Preference of Localized Structure for the C-H Bridged Carbocation2004

    • Author(s)
      H.Kawai
    • Journal Title

      Tetrahedron Letters 45・23

      Pages: 4553-4558

    • NAID

      130005010984

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Positive Homotropic Allosteric Binding of Benzenediols in a Hydrindacene-Based Exoditopic Receptor : Cooperativity in Amide Hydrogen Bonding2004

    • Author(s)
      H.Kawai
    • Journal Title

      Journal of the American Chemical Society 126・16

      Pages: 5034-5035

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Three-Way-Output Response System by Electric Potential : UV-Vis, CD and Fluorescence Spectral Changes upon Electrolysis of the Chiral Ester of Tetracyanoanthraquinodimethane2004

    • Author(s)
      H.Higuchi
    • Journal Title

      Tetrahedron Letters 45・15

      Pages: 3027-3030

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Pyrazino-Tetracyanonaphthoquinodimethanes : Non-Planar Electron Acceptors Affording Zwitterionic Neutral Radicals2004

    • Author(s)
      T.Suzuki
    • Journal Title

      Tetrahedron 60・9

      Pages: 1997-2003

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Preparation, Properties and X-ray Structures of 5,5'-Bi(8-aminoquinoxalyl)s : Novel Wurster-Type Electron Donors with a Heterobiaryl Skeleton2004

    • Author(s)
      T.Suzuki
    • Journal Title

      Tetrahedron Letters 45・2

      Pages: 329-333

    • Related Report
      2004 Annual Research Report

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Published: 2004-04-01   Modified: 2016-04-21  

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