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Development of Controlled Polymerization Based on Catalytic Cycloaddition Reactions

Research Project

Project/Area Number 25288057
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Polymer chemistry
Research InstitutionKanagawa University

Principal Investigator

Okamoto Sentaro  神奈川大学, 工学部, 教授 (00201989)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥8,840,000 (Direct Cost: ¥6,800,000、Indirect Cost: ¥2,040,000)
Fiscal Year 2015: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2013: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Keywords重合触媒 / 高分子合成 / 機能性高分子 / 触媒設計・反応
Outline of Final Research Achievements

Unprecedented chain-growth polymerizations based on catalytic cycloaddition reactions were developed. Polymerizations of diyne-alkyne AB monomers by catalysis in the presence of ClCl2/dipimp/Zn underwent in a chain-growth fashion to give polymers with narrow polydispersity. By control the reactivity of monomers, one-shot spontaneous block, random, or gradient polymerizations of two different monomers were realized. The method is also applicable to prepare conjugated polymers. The polymerization reaction proceeds through a catalyst-transfer mechanism, in which selection of a ligand for the catalyst complex is important. In addition, alkyne/nitrile [2+2+2] cycloaddition polymerization and diyne/ene [4+2] cycloaddition polymerization were investigated. These polymerization proceeded smoothly to afford the corresponding linear polymers but with wider polydispersity.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Annual Research Report
  • 2013 Annual Research Report
  • Research Products

    (31 results)

All 2016 2015 2014 2013 Other

All Journal Article (14 results) (of which Peer Reviewed: 13 results,  Acknowledgement Compliant: 2 results) Presentation (17 results) (of which Int'l Joint Research: 1 results,  Invited: 1 results)

  • [Journal Article] Catalytic [2 + 2 + 2] Cycloaddition Polymerization of Diyne-Nitrile Monomers in the Presence of CoCl2-6H2O/Diphosphine/Zn2016

    • Author(s)
      Yu-ki Sugiyama, Sentaro Okamoto
    • Journal Title

      J. Polym. Sci. A: Polym. Chem.

      Volume: 54 Issue: 3 Pages: 345-351

    • DOI

      10.1002/pola.27780

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed Reductive Metalation-Allylation and Metalative Cyclization of 2,3-Disubstituted Oxetanes and Their Stereoselectivity2016

    • Author(s)
      Yu-ki Sugiyama, Shiori Heigozono, Kazuhiro Tamura, Sentaro Okamoto
    • Journal Title

      Synthesis

      Volume: 印刷中

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Preparation of 2-hydroxy A-ring precursors for synthesis of vitamin D3 analogues from lyxose2015

    • Author(s)
      Kouta Ibe, Haruko Aoki, Hiromasa Takagi, Kiyohide Ken-mochi, Yu-suke Hasegawa, Naoto Hayashi, and Sentaro Okamoto
    • Journal Title

      Tetrahedron Letters

      Volume: 56 Issue: 18 Pages: 2315-2318

    • DOI

      10.1016/j.tetlet.2015.03.064

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed Reductive Magnesiation of Oxetanes to Gen-erate (3-Oxidopropyl)magnesium Reagents2014

    • Author(s)
      Yu-ki Sugiyama, Shiori Heigozono, and Sentaro Okamoto
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 24 Pages: 6278-6281

    • DOI

      10.1021/ol503191w

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Simple and practical method for selective acylation of primary hydroxy group catalyzed by N-methyl-2-phenylimidazole (Ph-NMI) or 2-phenylimidazo[2,1-b]benzothiazoles (Ph-IBT)2014

    • Author(s)
      Kouta Ibe, Yu-suke Hasegawa, Misuzu Shibuno, Tsukasa Shishido, Yuzo Sakai, Yu Kosaki, Keisuke Susa, and Sentaro Okamoto
    • Journal Title

      Tetrahedron Letters

      Volume: 55 Issue: 51 Pages: 7039-7042

    • DOI

      10.1016/j.tetlet.2014.10.130

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 有機金蔵触媒反応による重合反応2014

    • Author(s)
      岡本専太郎
    • Journal Title

      高分子

      Volume: 63 Pages: 654-657

    • Related Report
      2014 Annual Research Report
  • [Journal Article] Design and synthesis of 2-(1,3-dialkoxy-2-methylpropan-2-yl)-1,3-diarylpropanes as tethering units for folded H-stacking polymers2014

    • Author(s)
      Moriai, R.; Naito, Y.; Nomura, R.; Funyu, S.; Ishitsuka, K.; Asano, N.; Okamoto, S.
    • Journal Title

      Tetrahedron Lett.

      Volume: 55 Pages: 2649-2653

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Structure-activity relationship of dihydroimidazo-, dihydropyrimido, tetrahydrodiazepino-[2,1-b]-thiazoles and -benzothiazoles as an acylation catalyst2014

    • Author(s)
      Okamoto, S.; Sakai, Y.; Watanabe, S.; Nishi, S.; Yoneyama, A.; Katsumata, H.; Kosaki, Y.; Sato, R.; Shiratori, M.; Shibuno, M.; Shishido, T.
    • Journal Title

      Tetrahedron Lett.

      Volume: 55 Pages: 1909-1912

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 低原子価チタン反応剤Ti(OR)4/Me3SiCl/Mgの開発と反応2014

    • Author(s)
      岡本専太郎
    • Journal Title

      有機合成化学協会誌

      Volume: 72 Pages: 382-392

    • NAID

      130004548589

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Generation of A Low-Valent Titanium from Titanatrane and Its Catalytic Reactions: Radical Ring Opening of Oxetanes2013

    • Author(s)
      Naoto Takekoshi, Kenji Miyashita, Noriaki Shoji, Sentaro Okamoto
    • Journal Title

      Adv. Synth. Catal.

      Volume: 355 Pages: 2151-2157

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Properties of Through-Space Conjugated Polymers Based on π–π Stacked 1,3- Biarylpropane Tethering Units2013

    • Author(s)
      Ryosuke Nomura, Ryota Moriai, Masaru Kudo, Tohru Hoshino, Jun-ichi Watanabe, Shigeaki Funyu, Ken-ich Ishitsuka, Sentaro Okamoto
    • Journal Title

      J. Polymer Science Part A: Polymer Chemistry

      Volume: 51 Pages: 3412-3419

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cobalt-Catalyzed Cross Addition of Silylacetylenes to Internal Alkynes2013

    • Author(s)
      Tetsuya Sakurada, Yu-ki Sugiyama, Sentaro Okamoto
    • Journal Title

      J. Org. Chem.

      Volume: 78 Pages: 3583-3591

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Grignard allylic substitution reaction catalyzed by 1,2,3-triazol-5-ylidene magnesium complexes2013

    • Author(s)
      Ryosuke Nomura, Yuji Tsuchiya, Hiroyuki Ishikawa, Sentaro Okamoto
    • Journal Title

      Tetrahedron Lett.

      Volume: 54 Pages: 1360-1363

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] From Development of Catalysts for Alkyne and Alkyne/Nitrile [2 + 2 + 2] Cycloaddition Reactions to Their Use in Polymerization Reactions2013

    • Author(s)
      Sentaro Okamoto, Yu-ki Sugiyama
    • Journal Title

      SYNLETT

      Volume: 24 Pages: 1044-1060

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Presentation] Extensive Application of Cobalt-Catalyzed [2+2+2] Cycloaddition of Alkynes and Nitriles2016

    • Author(s)
      Yu-ki SUGIYAMA, Yukihiro ENDO, Miki IKARASHI, Chikashi MTSUNO, Sentaro OKAMOTO
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] Iron-catalyzed reductive magnesiation of oxetanes and metalative cyclization of alkynyl oxetanes2015

    • Author(s)
      Yuhki Tanabe, Yu-ki Sugiyama, Shiori Heigozono, Kazuhiro Tamura, Sentaro Okamoto
    • Organizer
      PacifiChem 2016
    • Place of Presentation
      Honolulu, Hawaii(米国)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 鉄触媒によるアルキニルオキセタンの分子内カルボメタル化反応2015

    • Author(s)
      清水めぐ・杉山雄樹・田村和大・松野千加士・岡本専太郎
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部(千葉)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 低原子価チタンによるAllocの脱保護法2015

    • Author(s)
      田邉雄己・高木啓允・松野千加士・岡本専太郎
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部(千葉)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 折り畳みπスタック高分子の光電変換素子への応用2015

    • Author(s)
      内藤佑輔・浅野直紀・舟生重昭・岡本専太郎
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部(千葉)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 鉄触媒3-オキシドプロピルマグネシウム反応剤の発生とその反応性2014

    • Author(s)
      杉山雄樹,藤本貴大,岡本専太郎
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学(福岡)
    • Year and Date
      2014-09-23 – 2014-09-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] 鉄触媒還元的マグネシウム化による3-オキシドプロピルマグネシウム反応剤の発生2014

    • Author(s)
      藤本貴大,杉山雄樹,平後園栞,岡本専太郎
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学(福岡)
    • Year and Date
      2014-09-23 – 2014-09-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] Iron-Catalyzed Reductive Magnesiation of Oxetanes Generating (3-Oxidopropyl)magnesium Reagents2014

    • Author(s)
      Sentaro Okamoto, Yu-ki Sugiyama, Takahiro Fujimoto, Shiori Heigozono
    • Organizer
      XXVI International Conference on Organometallic Chemistry (ICOMC 2014)
    • Place of Presentation
      札幌(北海道)
    • Year and Date
      2014-07-14 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] エーテル結合型折り畳みH-スタッキング高分子の合成2014

    • Author(s)
      内藤佑輔,森合亮太,舟生重昭,石塚健一,浅野直紀,岡本専太郎
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] 19-nor型ビタミンD誘導体A環部の合成法2014

    • Author(s)
      伊部公太,高木啓允,岡本専太郎
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] 低原子価アルコキシチタンによる脱アリル化・脱プロパルギル化反応2014

    • Author(s)
      高木啓允,田邊雄己,松野千加士,岡本専太郎
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] 種々の低原子価アルコキシチタンの発生と反応2014

    • Author(s)
      田邊雄己,竹腰直人,松野千加士,岡本専太郎
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] 鉄触媒によるオキセタン類の還元反応2014

    • Author(s)
      藤本貴大,杉山雄樹,平後園栞,岡本専太郎
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] 折り畳み型π積層高分子の合成と物性2013

    • Author(s)
      森合亮太, 内藤佑輔, 舟生重昭, 石塚健一, 浅野直紀, 岡本専太郎
    • Organizer
      第62回高分子討論会
    • Place of Presentation
      金沢大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] コバルト触媒シリルアセチレンの内部アルキンへの付加反応2013

    • Author(s)
      杉山雄樹, 桜田哲哉, 岡本専太郎
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] チタナトランからの低原子科チタン種の発生とその触媒反応2013

    • Author(s)
      竹腰直人, 宮下賢司, 正路則明, 松野千加士, 岡本専太郎
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] 均一系低原子価チタン反応剤の発生とその触媒的利用

    • Author(s)
      岡本専太郎
    • Organizer
      触媒学会横浜地区講演会
    • Place of Presentation
      神奈川大学
    • Related Report
      2013 Annual Research Report
    • Invited

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Published: 2013-05-21   Modified: 2019-07-29  

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