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Poly[3]rotaxane : Synthesis and Property of The Novel Polymer

Research Project

Project/Area Number 15350072
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Polymer chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

TAKATA Toshikazu  Tokyo Institute of Technology, Department of Organic and Polymeric Materials, Professor, 大学院・理工学研究科, 教授 (40179445)

Project Period (FY) 2003 – 2005
Project Status Completed (Fiscal Year 2005)
Budget Amount *help
¥15,100,000 (Direct Cost: ¥15,100,000)
Fiscal Year 2005: ¥3,000,000 (Direct Cost: ¥3,000,000)
Fiscal Year 2004: ¥4,300,000 (Direct Cost: ¥4,300,000)
Fiscal Year 2003: ¥7,800,000 (Direct Cost: ¥7,800,000)
Keywordspolyrotaxane / poly[3]rotaxane / dynamic covalent chemistry / polyrotaxane network / rotaxane / polymer sythesis / thiol-disulfide interchange / topological gel / 合成 / 可逆的開裂 / チオール-ジスルフィド交換反応 / リサイクル特性 / 還元反応 / ポリ[3]ロタキサン / チオールジスルフィド交換反応
Research Abstract

The present research has been carried out to study the synthesis and property of novel polymer "poly[3]rotaxane" by using protocol of reversible covalent bond cleavage. A dumbbell molecule was designed as an axle component which contained two secondary ammonium moieties on it and two bulky groups at the termini, by using thiol-disulfide interchange reaction. A mixture of the dumbbell molecule and a isophthaloyl diamide possessing two dibenzo-24-crown-8-ether moieties was treated with a catalytic amount of benzenethiol to give 65% yield of poly[3]rotaxane with Mn 25000. The effects of the structures of the components, solvent, catalyst, and concentration on the polymerization were studied in detail. When the axle component having longer alkyl chain was employed, the polymerization was sluggish to require much longer reaction time (more than 1 week) to reach the equilibrium. However, the molecular weight of the resulting polymers were higher than that from shorter alkyl chain derivative, … More probably because of the suppression of the formation of 1:1 adduct of the two componets, i.e. the axle and wheel monomers.
Thermal analyses and decomposition of poly[3]rotaxane were examined. Glass transition temperature and 5% weight loss temperature were 140℃ and 330℃, respectively, as determined by TGA and DSC analyses. Poly[3]rotaxane was treated with triohenylphosphine-water system as a typical reducing system for disulfide, and the corresponding reduced form of the dumbbell (a thiol) and the homofitopic crown ether (the wheel molecule) as the starting materials were recovered, suggesting the recycling property of poly[3]rotaxane.
The synthetic method of poly[3]rotaxane was extended to the corresponding network polymer, polyrotaxane network. Poly(crown ether) was used instead of the homoditopic crown ether resulted in the formation of solvent-insoluble gel material which was well swelled in DMF by the reaction with the dumbbell molecule. The gelled polymer as polyrotaxane network was translucent when dried but transparent when swelled in DMF. The property of the elastic swelled gel was controllable by changing the conditions, monomer feed ratio, concentration, solvent and so on Less

Report

(4 results)
  • 2005 Annual Research Report   Final Research Report Summary
  • 2004 Annual Research Report
  • 2003 Annual Research Report
  • Research Products

    (31 results)

All 2006 2005 2004 2003 Other

All Journal Article (21 results) Book (4 results) Patent(Industrial Property Rights) (2 results) Publications (4 results)

  • [Journal Article] Solid-State End-Capping of Pseudopolyrotaxane Possessing Hydroxy-Terminated Axle to Polyrotaxane and Its Application to the Synthesis of a Functionalized Polyrotaxane Capable of Yielding a Polyrotaxane Network2005

    • Author(s)
      Nobuhiro Kihara, Kazuma Hinoue, Toshikazu Takata
    • Journal Title

      Macromolecules 38

      Pages: 223-226

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Modification of Rotaxane by Suzuki-Miyaura-Type Coupling Reaction on the Axle Terminal2005

    • Author(s)
      N.Kihara, S.Motoda, T.Asakawa, T.Yokozawa, T Takata
    • Journal Title

      Org.Lett. 7・7

      Pages: 1199-1202

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Efficient Synthesis of [2] and [3] Rotaxanes via Transition Metal-catalyzed Hydrosilylation of Alkyne2005

    • Author(s)
      H.Sasabe, N.Kihara, Kazuhiko Mizuno, A.Ogawa, T.Takata
    • Journal Title

      Tetrahedron Lett. 46・22

      Pages: 3851-3853

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis and Photoinduced Electron Transfer Processes of Rotaxanes Bearing [60]Fullerene and Zinc Porphyrin : Effects of Interlocked Structure and Length of Axle with Porphyrins2005

    • Author(s)
      A.S.D.Sandanayaka, N.Watanabe, K.Ikeshita, Y.Araki, N.Kihara, Y.Furusho, O.Ito, T.Takata
    • Journal Title

      J.Phys.Chem., B 109

      Pages: 2516-2524

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Novel Concept for Recyclable Crosslinked Polymer : Topologically Networked Polyrotaxane Capable of Undergoing Reversible Crosslinking and Decrosslinking2004

    • Author(s)
      T.Oku, Y.Furusho, T.Takata
    • Journal Title

      Angew. Chem. Int. Ed. 43

      Pages: 966-969

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Dynamic Covalent Chemistry in Rotaxane Synthesis. Slipping Approach to [2]Rotaxane Utilizing Reversible Cleavage-Rebondage of Trityl Thioether Linkage2004

    • Author(s)
      Y.Furusho, T.Oku, G.A.Rajkumar, T.Takata
    • Journal Title

      Chem. Lett. 33

      Pages: 52-53

    • NAID

      10011943436

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Novel Concept for Recyclable Crosslinked Polymer : Topologically Networked Polyrotaxane Capable of Undergoing Reversible Crosslinking and Decrosslinking2004

    • Author(s)
      T.Oku
    • Journal Title

      Angew.Chem.Int.Ed. 43

      Pages: 966-969

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Dynamic Covalent Chemistry in Rotaxane Synthesis. Slipping Approach to [2]Rotaxane Utilizing Reversible Cleavage-Rebondage of Trityl Thioether Linkage2004

    • Author(s)
      Y.Furuaho
    • Journal Title

      Chem.Lett. 33

      Pages: 52-53

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Polymer Synthesis2004

    • Author(s)
      T.Takata
    • Journal Title

      Adv.Polym.Sci. (Springer)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Novel Concept for Recyclable Crosslinked Polymer : Topologically Networked Polyrotaxane Capable of Undergoing Reversible Crosslinking and Decrosslinking2004

    • Author(s)
      Tomoya Oku, Yoshio Furusho, Toshikazu Takata
    • Journal Title

      Angew.Chem.Int.Ed. 43[3]

      Pages: 966-969

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Synthesis of [2]- and [3]Rotaxanes by End-Capping Approach Utilizing Urethane Formation2004

    • Author(s)
      Yoshio Furusho, Hisahiro Sasabe, Daisuke Natsui, Ken-ichi Murakawa, Toshiro Harada, Toshikazu Takata
    • Journal Title

      Bull.Chem.Soc.Jpn. 77[1]

      Pages: 179-185

    • NAID

      10011836245

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Dynamic Covalent Chemistry in Rotaxane Synthesis. Slipping Approach to [2]Rotaxane Utilizing Reversible Cleavage Rebondage of Trityl Thioether Linkage2004

    • Author(s)
      Yoshio Furusho, Tomoya Oku, G.Abraham Rajkumar, Toshikazu Takata
    • Journal Title

      Chem.Lett 33[1]

      Pages: 52-53

    • NAID

      10011943436

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Bridged Polycatenane2004

    • Author(s)
      Nobuhiro Watanabe, Yoshihiro Ikari, Nobuhiro Kihara, Toshikazu Takata
    • Journal Title

      Macromolecules 37[18]

      Pages: 6663-6666

    • NAID

      130005010936

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Synthesis and Shuttling Behavior of Rotaxanes Consisting of Crown Ether Wheel and Disulfide Dumbbell with Two Ammonium Center2004

    • Author(s)
      Yoshio Furusho, Ryoko Sannoh, Tomoya Oku, Toshikazu Takata
    • Journal Title

      Bull.Korean Chem.Soc 25

      Pages: 1641-1644

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Synthesis of Side-Chain Polyrotaxane by Radical Polymerizations of Vinylic Pseudorotaxane Monomers Having Paraquat Type Macrocycle as a Wheel Component2004

    • Author(s)
      Toshikazu Takata, Toshihide Hasegawa, Nobuhiro Kihara, Yoshio Furusho
    • Journal Title

      Polym.J. 36

      Pages: 927-932

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Dynamic Covalent Approach to [2]- and [3]Rotaxanes by Utilizing the Reversible Thiol-Disulfide Interchange Reaction2003

    • Author(s)
      Y.Furusho, T.a Oku, T.Hasegawa, A.Tsuboi, N.Kihara, T.Takata
    • Journal Title

      Chem. Eur. J. 9

      Pages: 2895-2903

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] First poly[3]rotaxane synthesized through the noncovalent step-growth polymerization of a homoditopic dumbbell compound and a macrocycle with a reversible thiol-disulfide interchange reaction2003

    • Author(s)
      T.Oku, Y.Furusho, T.Takata
    • Journal Title

      J. Polym. Sci., Polym. Chem., Rapid Commun. 41

      Pages: 119-123

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Rotaxane-Stabilized Thiophosphonium Salt from Disulfide and Phosphine2003

    • Author(s)
      T.Oku, Y.o Furusho, T.Takata
    • Journal Title

      Org. Lett. 5

      Pages: 4923-4925

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Dynamic Covalent Approach to [2]- and [3]Rotaxanes by Utilizing the Reversible Thiol-Disulfide Interchange Reaction2003

    • Author(s)
      Y.Furusho
    • Journal Title

      Chem.Eur.J. 9(12)

      Pages: 2895-2903

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] First poly[3]rotaxane synthesized through the noncovalent step-growth polymerization of a homoditopic dumbbell compound and a macrocycle with a reversible thiol-disulfide interchange reaction2003

    • Author(s)
      T.Oku
    • Journal Title

      J.Polym.Sci., Polym.Chem., Rapid Commun. 41[1]

      Pages: 119-123

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Rotaxane-Stubilized Thiophosphonium Salt from Disulfide and Phosphine,2003

    • Author(s)
      T.Oku
    • Journal Title

      Org.Lett. 5[26]

      Pages: 4923-4925

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Book] 環状・筒状超分子新素材の応用技術(第1章、環・筒・管の特性を活かした超分子材料)(高田十志和監修)2006

    • Author(s)
      高田十志和
    • Total Pages
      246
    • Publisher
      シーエムシー出版
    • Related Report
      2005 Annual Research Report
  • [Book] Polymer Synthesis2004

    • Author(s)
      T.Takata, N.Kihara, Y.Furusho
    • Total Pages
      213
    • Publisher
      Springer
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Book] 高分子科学(第20章、ロタキサン、ポリロタキサンの戦略的設計・合成)、中嶋直敏編2004

    • Author(s)
      高田十志和
    • Publisher
      化学同人
    • Related Report
      2004 Annual Research Report
  • [Book] Polyrotaxanes and Polycatenanes : Recent Advances in Syntheses and Applications of Polymers Comprising of Interlocked Structure2004

    • Author(s)
      Toshikazu Takata, Nobuhiro Kihara, Yoshio Furusho
    • Publisher
      Adv.Polym.Sci.
    • Related Report
      2004 Annual Research Report
  • [Patent(Industrial Property Rights)] 高田十志和2005

    • Inventor(s)
      国立大学法人東京工業大学
    • Industrial Property Rights Holder
      特願2005-261530
    • Filing Date
      2005-09-15
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 特許2005

    • Inventor(s)
      高田 十志和, 松山 剛知, 渡辺 将浩
    • Industrial Property Rights Holder
      東京工業大学
    • Industrial Property Number
      2005-261530
    • Filing Date
      2005-09-14
    • Related Report
      2005 Annual Research Report
  • [Publications] Yoshio Furusho, Toshikazu Takata ほか: "Novel Concept for Recyclable Crosslinked Polymer : Topologically Networked Polyrotaxane Capable of Undergoing Reversible Crosslinking and Decrosslinking"Angew.Chem.Int.Ed.. 43. 966-969 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] Yoshio Furusho, Toshikazu Takata ほか: "First Poly[3]rotaxane synthesized through the noncovalent step-growth polymerization of a homoditopic dumbbell compound and a macrocvcle with a reversible..."J.Polym.Sci., Polym.Chem., Rapid Commun.. 41. 119-123 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Yoshio Furusho, Toshikazu Tahaka ほか: "Dynamic Covalent Approach to [2]- and [3]Rotaxanes by Utilizing the Reversible Thiol-Disulfide Interchange Reaction"Chem.Eur.J.. 9. 2895-2903 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] 高田 十志和: "超分子科学"化学同人(印刷中). (2004)

    • Related Report
      2003 Annual Research Report

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Published: 2003-04-01   Modified: 2016-04-21  

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