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Synthesis of Polypropellanes via Ring-Opening Polymerization or Coupling Reaction

Research Project

Project/Area Number 14550833
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 高分子合成
Research InstitutionTokyo Institute of Technology

Principal Investigator

ISHIZONE Takashi  Tokyo Institute of Technology, Department of Organic and Polymeric Materials, Associate Professor, 大学院・理工学研究科, 助教授 (60212883)

Project Period (FY) 2002 – 2004
Project Status Completed (Fiscal Year 2004)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2004: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2003: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2002: ¥2,200,000 (Direct Cost: ¥2,200,000)
KeywordsPropellane / Ring-opening polymerization / 1,3-Dehydroadamantane / Poly(1,3-adamantane) / Cationic polymerization / Alternating copolymerization / Ring strain / Coupling reaction / 1,3-デヒドロアダマンタ / ラジカル重合 / ブロペラン
Research Abstract

Cationic ring-opening polymerizations of [3.3.1]propellane derivatives, 1,3-dehydroadamantane (1)and 5-butyl-1,3-dehydroadamantane (2), were carried out with CF_3SO_3H in CH_2Cl_2 at 0℃ for 6-42 h. The central σ-bonds in 1 and 2 were exclusively opened to afford novel poly([3.3.1]propellane)s, poly(1,3-adamantane)s, in good to quantitative yields. The resulting poly(2)possessing flexible butyl substituent was soluble in chloroform, THF, and 1,2-dichlorobenzene, and the degree of polymerization was estimated to be greater than 30, while the poly(1)was hardly soluble in the common organic solvents. All aliphatic poly(1)and poly(2)showed high thermal stability, whose 10% weight loss temperatures were 421 and 486℃, respectively.

Report

(4 results)
  • 2004 Annual Research Report   Final Research Report Summary
  • 2003 Annual Research Report
  • 2002 Annual Research Report
  • Research Products

    (30 results)

All 2004 2003 2002 Other

All Journal Article (20 results) Publications (10 results)

  • [Journal Article] Synthesis of well-defined block copolymers containing poly(N-isopropylacrylamide) segment by anionic block copolymerization of N-methoxymethyl-N-isopropylacrylamide2004

    • Author(s)
      Mana Ito, Takashi Ishizone
    • Journal Title

      Desingned Monomers and Polymers 7

      Pages: 11-24

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] 官能基を有する極性モノマー類のリビングアニオン重合2004

    • Author(s)
      石曽根隆, 伊藤まな, 小林真盛
    • Journal Title

      日本接着学会誌 40

      Pages: 407-414

    • NAID

      10014289412

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Annual Research Report 2004 Final Research Report Summary
  • [Journal Article] Synthesis of Poly(1,3-adamantane)s by Cationic Ring-Opening Polymerization of 1,3-Dehydroadamantanes2004

    • Author(s)
      Takashi Ishizone, Shin-ichi Mastuoka, Shiko Sakai, Wataru Harada, Hiroyuki Tajima
    • Journal Title

      Macromolecules 37

      Pages: 7069-7071

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] アダマンタン骨格を含む高分子の合成2004

    • Author(s)
      石曽根隆
    • Journal Title

      高分子 53

      Pages: 342-347

    • NAID

      10012903644

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis of Polymers Containing Adamantne Skeleton2004

    • Author(s)
      Takashi Ishizone
    • Journal Title

      Kobunshi 53, (5)

      Pages: 342-347

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis of Poly(1,3-adamantane)s by Cationic Ring-Opening Polymerization of 1,3-Dehydroadamantanes2004

    • Author(s)
      Takashi Ishizone, Shin-ichi Matsuoka, Shiko Sakai, Wataru Harada, Hiroyuki Tajima
    • Journal Title

      Macromolecules 37, (19)

      Pages: 7069-7071

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Living Anionic Polymerization of Polar Monomers Containing Functional Groups2004

    • Author(s)
      Takashi Ishizone, Mana Ito, Mamoru Kobayashi
    • Journal Title

      Journal of the Adhesion Society of Japan 40, (9)

      Pages: 407-414

    • NAID

      10014289412

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis of well-defined block copolymers containing poly(N-isopropylacrylamide) segment by anionic block copolymerization of N-methoxymethyl-N-isopropylacrylamide2004

    • Author(s)
      Mana Ito, Takashi Ishizone
    • Journal Title

      Designed Monomers and Polymers 7, (1-2)

      Pages: 11-24

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis of well-defined block copolymers containing poly(N-isopropylacrylamide) segment by anionic block copolymerization of N-methoxymethyl-N-isopropylacrylamide2004

    • Author(s)
      Mana Ito, Takashi Ishizone
    • Journal Title

      Designed Monomers and Polymers 7

      Pages: 11-24

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Synthesis of Poly(1,3-adamantane)s by Cationic Ring-Opening Polymerization of 1,3-Dehydroadamantanes2004

    • Author(s)
      Takashi Ishizone, Shin-ichi Matsuoka, Shiko Sakai, Wataru Harada, Hiroyuki Tajima
    • Journal Title

      Macromolecules 37

      Pages: 7069-7071

    • Related Report
      2004 Annual Research Report
  • [Journal Article] アダマンタン骨格を含む高分子の合成2004

    • Author(s)
      石曽根 隆
    • Journal Title

      高分子 53

      Pages: 342-347

    • NAID

      10012903644

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Anionic Polymerization of 2-Haloethyl Methacrylates2003

    • Author(s)
      Kenji Sugiyama, Hiroko Azuma, Takumi Watanabe, Takashi Ishizone. Akira Hirao
    • Journal Title

      Polymer 44

      Pages: 4157-4164

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Anionic Polymerization of p-Pentamethyldisilyl-, p-Heptamethyltrisilyl-, p-Nonamethyl tetrasilyl styrenes2003

    • Author(s)
      Akira Hirao, Yushi Ando, Takashi Ishizone, Seiichi Nakahama
    • Journal Title

      Macromolecules 36, (14)

      Pages: 5081-5087

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis of New Crosslinkable Polymers by Chemoselective Polymerizations of 2-(1-Aziridinyl)ethyl Methacrylate2003

    • Author(s)
      Takashi Ishizone.Tadahiro Takata, Mamoru Kobayashi
    • Journal Title

      J.Polym.Sci., Part A, Polym.Chem. 41

      Pages: 1335-1340

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis of Water-soluble Polymethacrylates by Living Anionic Polymerization of Trialkylsilyl-Protected Oligo(ethylene glycol) Methacrylates2003

    • Author(s)
      Takashi Ishizone.Seok Han, Syunsuke Okuyama, Seiichi Nakahama
    • Journal Title

      Macromolecules 36

      Pages: 42-49

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis of Thermally Sensitive Water-Soluble Polymethacrylates by Living Anionic Polymerizations of Oligo(ethylene glycol) Methyl Ether Methacrylates2002

    • Author(s)
      Seok Han, Mamoru Hagiwara, Takashi Ishizone
    • Journal Title

      Macromolecules 36, (22)

      Pages: 8312-8319

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Anionic Polymerizations of 1-Adamantyl Methacrylate and 3-Methacryloyloxy-1,1'-biadamantane2002

    • Author(s)
      Takashi Ishizone.Hiroyuki Tajima, Hiroshi Torimae, Seiichi Nakahama
    • Journal Title

      Macromol Chem.Phys. 203

      Pages: 2375-2384

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis of Well-Defined Poly(N-isopropylacrylamide) by the Anionic Polymerization of N-Methoxymethyl-N-isopropylacrylamide2002

    • Author(s)
      Takashi Ishizone, Mana Ito
    • Journal Title

      J.Polym.Sci., Part A, Polym.Chem. 40

      Pages: 4328-4332

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Recent Advance in Living Anionic Polymerization of Functionalized Styrene Derivatives2002

    • Author(s)
      Akira Hirao, Surapich Loykulnant, Takashi Ishizone
    • Journal Title

      Prog.Polym.Sci. 27

      Pages: 1399-1471

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis of Well-Defined Polymers End-Functionalized with Cross-linkable Aziridine Groups by Living Anionic Polymerization

    • Author(s)
      Mamoru Kobayashi, Kentaro Uchino, Takashi Ishizone
    • Journal Title

      J.Polym.Sci., Part A, Polym.Chem. (印刷中)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Publications] S.Han, M.Hagiwara, T.Ishizone: "Synthesis of Thermally-sensitive Water-soluble Polymethacrylates by Living Anionic Polymerization of Oligo(ethylene glycol) Methyl Ether Methacrylates"Macromolecules. 36. 8312-8319 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] K.Sugiyama, H.Azuma, T.Watanabe, T.Ishizone, A.Hirao: "Anionic Polymerization of 2-Haloethyl Methacrylates"Polymer. 44. 4157-4164 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] A.Hirao, Y.Ando, T.Ishizone, S.Nakahama: "Anionic Polymerization of p-Pentamethyldisilyl-, p-Heptamethyltrisilyl-, and p-Nonamethyltetrasilylstyrenes"Macromolecules. 36. 5081-5087 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] T.Ishizone, T.Takata, M.Kobayashi: "Synthesis of New Crosslinkable Polymers by Chemoselective Polymerizations of 2-(1-Aziridinyl)ethyl Methacrylate"J.Polym.Sci., Part A, Polym.Chem.. 41. 1335-1340 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] T.Ishizone, S.Han, S.Okuyama, S.Nakahama: "Synthesis of Water-soluble Polymethacrylates by Living Anionic Polymerization of Trialkylsilyl- protected Oligo(ethylene glycol) Methacrylates"Macromolecules. 36. 42-49 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] 田島寛之, 石曽根隆: "アダマンタン骨格を含むポリマー類の合成"高分子加工. 51・3. 98-104 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] A.Hirao, S.Loykulnant, T.Ishizone: "Recent advance in living anionic polymerization of functionalized styrene derivatives"Progress in Polymer Science. 27. 1399-1471 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] T.Ishizone, H.Tajima, H.Torimae.S.Nakahama: "Anionic Polymerization of 1-Adamanryl Methacrylate and 3-Methacryloyloxy-1,1'-biadamantane"Macromolecular Chemistry and Physics. 203・16. 2375-2384 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] T.Ishizone, M.Ito: "Synthesis of Well-Defined Poly(N-isopropylacrylamide) by the Anionic Polymerization of N-Methoxymethyl-N-isopropylacrylamide"Rapid Communication. 40. 4328-4332 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] T.Ishizone, S.Han, S.Okuyama.S.Nakahama: "Synthesis of Water-Soluble Polymethacrylates by Living Anionic Polymerization of Trialkylsilyl-Protected Oligo(ethylene glycol)Methacrylates"Macromolecules. 36・1. 42-49 (2003)

    • Related Report
      2002 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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