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Synthetic study on phosphorus analog of polyaniline bearing sterically protected phosphorus atoms of high p-character as key structures

Research Project

Project/Area Number 25600020
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Nanomaterials chemistry
Research InstitutionTohoku University

Principal Investigator

Sasaki Shigeru  東北大学, 理学(系)研究科(研究院), 助教 (90254143)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
Fiscal Year 2015: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2014: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2013: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Keywordsリン / ポリアニリン / 立体保護 / 1級ホスフィン / 2級ホスフィン / クロロホスフィン / ホスホン酸ジエステル / クロスカップリング反応 / ホスフィン / ジクロロホスフィン / 還元 / 遷移金属錯体触媒 / クロスカップリング / ジアリールホスフィン / ブロモ基 / ターフェニル / 合成中間体 / 重合反応 / 光分解
Outline of Final Research Achievements

The trivalent phosphorus atoms bearing bulky aryl groups have high p-character arising from the structural change around the phosphorus and sterically protected environment. In this project, diaryphosphine moieties bearing bulky aryl groups are employed as key structures for the phosphorus analogs of polyaniline to improve instability of the phosphine moieties and lack of the effective π-conjugation due to low p-character of the phosphorus atom, and synthetic studies on the substructures and polymers were carried out.
Diarylphosphines substituted by 2,6-disubstituted aryl group and various 4-bromoaryl groups were synthesized by the nucleophilic substitution of the corresponding dichlorophosphine followed by the reduction. 4-Bromophenylphosphines bearing bulky alkyl or aryl groups at 2,6-positions were synthesized by the reduction of the corresponding dichlorophosphines or diethyl phosphonates prepared from bromoiodobenzene derivatives, and reactivities were studied.

Report

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

    (13 results)

All 2016 2015 2014 2013

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Acknowledgement Compliant: 2 results) Presentation (10 results) (of which Int'l Joint Research: 1 results)

  • [Journal Article] Synthesis and properties of a sterically crowded triarylphosphine bearing an ester group2016

    • Author(s)
      Shigeru Sasaki and Masaaki Yoshifuji
    • Journal Title

      Phosphorus, Sulfur Silicon Relat. Elem.

      Volume: 191 Issue: 3 Pages: 507-510

    • DOI

      10.1080/10426507.2015.1114943

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis, structure, and properties of [4-methyl-2,6-bis(2-methylphenyl)phenyl]bis(2,4,6-triisopropylphenyl)phosphine2015

    • Author(s)
      Shigeru Sasaki, Yusuke Shimizu, and Masaaki Yoshifuji
    • Journal Title

      Phosphorus, Sulfur Silicon Relat. Elem.

      Volume: accepted Issue: 5-6 Pages: 672-676

    • DOI

      10.1080/10426507.2014.984031

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and structure of sterically crowded triarylphosphine bearing 4-bromo-2,6-bis(4-tert-butylphenyl)phenyl group2014

    • Author(s)
      Shigeru Sasaki, Masatoshi Izawa, and Masaaki Yoshifuji
    • Journal Title

      Phosphorus, Sulfur Silicon Relat. Elem.

      Volume: accepted

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 4-ブロモアリール基を有する立体保護されたホスフィン類の合成と反応2016

    • Author(s)
      佐々木 茂
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学 京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Sterically crowded triarylphosphines and their material oriented derivatives2015

    • Author(s)
      Shigeru Sasaki, Noboru Morita, and Masaaki Yoshifuji
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies (Pacifichem 2015)
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 4-ブロモアリール基を有する立体保護されたジアリールホスフィン誘導体の合成と反応2015

    • Author(s)
      佐々木 茂
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学/理工学部船橋キャンパス・薬学部、船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] 立体混雑したトリアリールホスフィンの一電子酸化及び酸素化反応2014

    • Author(s)
      佐々木 茂
    • Organizer
      第25回基礎有機化学討論会(第44回構想有機化学討論会/第64回有機反応化学討論会)
    • Place of Presentation
      東北大学川内北キャンパス・萩ホール、仙台
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Research-status Report
  • [Presentation] Structures and Reactivities of Sterically Crowded Triarylphosphines, Arsines, and Their Radical Cations2014

    • Author(s)
      Shigeru SASAKI, Masatoshi IZAWA, Yukihiro YAMAMOTO, Kiyotoshi KATO, Yusuke SHIMIZU, Katsuhide SUTOH, and Masaaki YOSHIFUJI
    • Organizer
      the XXVI International Conference on Organometallic Chemistry (ICOMC 2014)
    • Place of Presentation
      Sapporo, Japan
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Research-status Report
  • [Presentation] Structures and Reactivities of Sterically Crowded Triarylphosphines and Their Derivatives2014

    • Author(s)
      Shigeru SASAKI, Masatoshi IZAWA, Yukihiro YAMAMOTO, Kiyotoshi KATO, Yusuke SHIMIZU, Katsuhide SUTOH, and Masaaki YOSHIFUJI
    • Organizer
      the 20th International Conference on Phosphorus Chemistry (ICPC2014)
    • Place of Presentation
      University College Dublin (UCD), Dublin, Ireland
    • Year and Date
      2014-06-28 – 2014-07-02
    • Related Report
      2014 Research-status Report
  • [Presentation] カルボニル基と共役した立体混雑したトリアリールホスフィンの合成、構造、性質2014

    • Author(s)
      佐々木 茂
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学・東山キャンパス(愛知県名古屋市)
    • Related Report
      2013 Research-status Report
  • [Presentation] 立体混雑した4,4’-ビス(ジホスフィノアリール)ケトンの合成、構造、性質2013

    • Author(s)
      佐々木茂
    • Organizer
      第24回基礎有機化学討論会(第43回構想有機化学討論会/第63回有機反応化学討論会)
    • Place of Presentation
      学習院大学目白キャンパス、創立百周年記念会館(東京都豊島区)
    • Related Report
      2013 Research-status Report
  • [Presentation] Structure and properties of derivatives of sterically crowded triarylphosphines and arsines2013

    • Author(s)
      Shigeru Sasaki, Katsuhide Sutoh, Kiyotoshi Kato, Yukihiro Yamamoto, Masatoshi Izawa, Yusuke Shimizu, Masaaki Yoshifuji, Noboru Morita
    • Organizer
      International Symposim for the 70th Anniversary of the Tohoku Branch of the Chemical Society of Japan
    • Place of Presentation
      東北大学川内キャンパス(宮城県仙台市)
    • Related Report
      2013 Research-status Report
  • [Presentation] チオカルボニル基を有する立体混雑したトリアリールホスフィンの合成、構造、性質2013

    • Author(s)
      佐々木 茂
    • Organizer
      第40回有機典型元素化学討論会
    • Place of Presentation
      近畿大学11月ホール(大阪府東大阪市)
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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