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The development of selective synthetic method of methanofullerene via flow-micro synthesis

Research Project

Project/Area Number 16K06851
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Reaction engineering/Process system
Research InstitutionOsaka Research Institute of Industrial Science and Technology (2017-2019)
Osaka Municipal Technical Research Institute (2016)

Principal Investigator

Iwai Toshiyuki  地方独立行政法人大阪産業技術研究所, 森之宮センター, 主任研究員 (20416291)

Co-Investigator(Kenkyū-buntansha) 伊藤 貴敏  地方独立行政法人大阪産業技術研究所, 森之宮センター, 総括研究員 (60416295)
Project Period (FY) 2016-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2018: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2017: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2016: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywordsマイクロリアクター / フロー合成 / フラーレン / メタノフラーレン / 有機薄膜太陽電池 / ヒドラゾン / 硫黄イリド
Outline of Final Research Achievements

The flow synthesis of methanofullerene derivative PCBM by the reaction of tosylhydrazone in aqueous two-phase system, and by the reaction of sulfur ylide generated from sulfonium salt was invesdtigated. In the attempt of tosylhydrazone in aqueous two-phase system, two flow reactors (heating unit and photo irradiation unit) were connected and PCBM was synthesized directly without the isolation of fulleroid. In the case of sulfur ylide method, the organic base was re-investigated for the flow synthesis, and the reaction was completed within a few second under the optimized flow condition. The attempts of flow synthesis of methanofullerene derivative PCBM using these two methods were successfully achieved under continuous flow condition.

Academic Significance and Societal Importance of the Research Achievements

フローマイクロ合成という手法は、混合が早い、温度制御が精密かつ容易、反応時間の精密制御が可能などの特長があり、有機合成化学の分野を中心に広く注目を集めており、実用化が期待されている技術である。また、小さなスケールから利用でき、必要な量だけ製造することも可能であるため、環境負荷低減にもつながる技術でもある。本研究成果は、PCBMのみならず、今後開発される可能性のある様々なメタノフラーレン誘導体の合成にも適用できるものであると考えており、有機薄膜太陽電池の開発、ひいてはエネルギー問題、環境問題の解決策にも資するものであるといえる。

Report

(5 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (7 results)

All 2020 2019 2018 2017 2016

All Presentation (7 results) (of which Int'l Joint Research: 4 results,  Invited: 1 results)

  • [Presentation] 水系二層系条件におけるフラーレン誘導体PCBMの連続フロー合成2020

    • Author(s)
      岩井 利之、隅野 修平、松元 深、伊藤 貴敏、大野 敏信
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Continuous Flow Synthesis of Methanofullerene Derivative PCBM Using in situ Generated Sulfur Ylide2019

    • Author(s)
      Toshiyuki Iwai, Takatoshi Ito, Shuhei Sumino, Fukashi Matsumoto, Toshinobu Ohno
    • Organizer
      2nd International Conference on Automated Flow and Microreactor Synthesis (ICAMS-2)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Two Methods for Continuous Flow Syntheses of Methanofullerene Derivative PCBM : Hydrazone in Aqueous Two-phase System and in situ Generated Sulfur Ylide System2018

    • Author(s)
      Toshiyuki Iwai, Takatoshi Ito, Shuhei Sumino, Fukashi Matsumoto, Takumi Mizuno, Toshinobu Ohno
    • Organizer
      第14回国際有機化学京都会議(IKCOC-14)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Flow Synthesis of Methanofullerene Derivative PCBM Using in situ Generated Sulfur Ylide2018

    • Author(s)
      Takatoshi Ito, Toshiyuki Iwai, Shuhei Sumino, Fukashi Matsumoto, Yuta Inoue, Tetsuo Iwasawa, Takumi Mizuno, Toshinobu Ohno
    • Organizer
      The First International Conference on Automated Flow and Microreactor Synthesis(ICAMS-1)
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] 硫黄イリド法を利用するメタノフラーレン誘導体(PCBM)合成の最適反応条件化2018

    • Author(s)
      伊藤貴敏、岩井利之、松元深、隅野修平、森脇和之、大野敏信
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] フロー反応による有機太陽電池用アクセプター材料:[70]PCBMの位置選択的合成法2017

    • Author(s)
      井上裕太、岩澤哲郎、伊藤貴敏、岩井利之、隅野修平、松元深、森脇和之、大野敏信
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス(神奈川県横浜市)
    • Year and Date
      2017-03-18
    • Related Report
      2016 Research-status Report
  • [Presentation] Efficient synthesis of [6,6]-phenyl-C61/71-butyric acid methyl esters (PCBMs) for bulk-heterojunction solar cell2016

    • Author(s)
      Takatoshi Ito, Fukashi Matsumoto, Toshiyuki Iwai, Kazuyuki Moriwaki, Yuko Takao, Takumi Mizuno, Toshinobu Ohno
    • Organizer
      International Conference on Novel Materials and Their Synthesis (NMS -XII)
    • Place of Presentation
      湖南農業大学(中国長沙市)
    • Year and Date
      2016-10-17
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited

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Published: 2016-04-21   Modified: 2021-02-19  

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