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Development of new functional materials based on hydroquinone dimers

Research Project

Project/Area Number 17H03023
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionYamaguchi University

Principal Investigator

KAMIMURA Akio  山口大学, 大学院創成科学研究科, 教授 (30194971)

Co-Investigator(Kenkyū-buntansha) 川本 拓治  山口大学, 大学院創成科学研究科, 助教 (70756139)
Project Period (FY) 2017-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥18,850,000 (Direct Cost: ¥14,500,000、Indirect Cost: ¥4,350,000)
Fiscal Year 2020: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Fiscal Year 2019: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Fiscal Year 2018: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Fiscal Year 2017: ¥8,710,000 (Direct Cost: ¥6,700,000、Indirect Cost: ¥2,010,000)
Keywords蛍光材料 / バイオイメージング / 水溶性 / ポリエチレングリコール / 大環状化合物 / ホストゲスト化学 / C3対称性 / アセタール
Outline of Final Research Achievements

Preparation of water-soluble 2-sulfanylhydroquinone dimer and derivatized it for a bio-imaging material. We succeeded to detect BSA protein as a model study using this derivative and showed it would be a potential photoluminescence compound for this purpose. We also developed selective demethylation reaction for its tetramethyl ether, and achieved one-step preparation of mono-methyl derivative. Its oxidation form, mono-quinone derivative, showed good photolumenscence when exposed to reductive conditions delivered by ascorbic acid, and found that it would be a potential compound serving as a new reagent for detection of reducing agents.
Several derivatives of deltaarene, a new macrocyclic compounds based on a 2-sulfanylhydroquinone dimer, were prepared and estimated their shape and size of the holes. We also examined several reactions towards their derivatization and chemical modification.

Academic Significance and Societal Importance of the Research Achievements

本研究により我々が開発した新規蛍光染料である2-スルファニルヒドロキノン二量体がバイオイメージング材料として利用可能であることを明らかにした。この成果は生化学分野に新しい検出材を提供することが期待され、この分野の発展に寄与する成果である。また新規大環状化合物のデルタアレーンの化学の基礎的な研究を進め、この化合物群を新しい分子ホストとして活用できる足がかりを得た。この成果も生化学をはじめ材料開発にも新しい方法論をもたらすことが期待できる。

Report

(5 results)
  • 2021 Final Research Report ( PDF )
  • 2020 Annual Research Report
  • 2019 Annual Research Report
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • Research Products

    (22 results)

All 2022 2021 2020 2019 2018 2017 Other

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Open Access: 1 results) Presentation (18 results) (of which Int'l Joint Research: 7 results,  Invited: 1 results) Remarks (1 results)

  • [Journal Article] Development of Water Solubility of 2-Phenylsulfanylhydroquinone Dimer Dye2021

    • Author(s)
      Kamimura Akio、Umemoto Haruka、Kawamoto Takuji、Honda Takeshi
    • Journal Title

      ACS Omega

      Volume: 6 Issue: 13 Pages: 9254-9262

    • DOI

      10.1021/acsomega.1c00703

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] 2‐Sulfanylhydroquinone Dimer as a Switchable Fluorescent Dye2019

    • Author(s)
      Kamimura Akio、Sakamoto Sanshiro、Umemoto Haruka、Kawamoto Takuji、Sumimoto Michinori
    • Journal Title

      Chemistry - A European Journal

      Volume: 25 Issue: 62 Pages: 14081-14088

    • DOI

      10.1002/chem.201903436

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Deltaarenes; novel macrocyclic molecules that are readily available from 1,4-benzoquinone and benzene dithiols2018

    • Author(s)
      Akio Kamimura,* Ryusuke Watanabe, Tomoki Fukumitsu, Kazuki Ikeda, Takuji Kawamoto, Michinori Sumimoto, Shigeki Mori, and Hidemitsu Uno
    • Journal Title

      Tetrahedron

      Volume: 74 Issue: 38 Pages: 5303-5308

    • DOI

      10.1016/j.tet.2018.04.070

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Presentation] 酸化還元に対応する蛍光材料:2-スルファニルヒドロキノン二量体の硫黄誘導体の合成と光物性2022

    • Author(s)
      吉井秀樹, 安部 航輝, 川本 拓治, 上村 明男
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 2-スルファニルヒドロキノン二量体蛍光色素の酸化還元応答2021

    • Author(s)
      安部航輝・川本拓治・上村明男
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ヒドロキノン二量体を使った新規材料の創成探索2021

    • Author(s)
      上村明男
    • Organizer
      2021年度第2回有機合成化学協会講演会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 酸化還元に応答してON/OFFする新規蛍光色素の開発2021

    • Author(s)
      安部 航輝, 川本 拓治, 上村 明男
    • Organizer
      第48回有機典型元素化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Development of a new bioimaging material based on 2-sulfanylhydroquinone dimer2021

    • Author(s)
      Akio Kamimura, Haruka Umemoto, Takuji Kawamoto, Takeshi Honda
    • Organizer
      Pacifichem2021
    • Related Report
      2019 Annual Research Report
  • [Presentation] 2-スルファニルヒドロキノン蛍光色素の位置選択的誘導化反応2020

    • Author(s)
      安部航輝・川本拓治・上村明男
    • Organizer
      第47回有機典型元素化学討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 2-スルファニルヒドロキノン蛍光色素の大量合成と位置選択的誘導化反応2020

    • Author(s)
      安部航輝, 川本拓治, 上村明男
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 2-スルファニルヒドロキノン誘導体蛍光材料のバイオイメージング材料に向けた展開2019

    • Author(s)
      梅本 春香, 川本 拓治, 本田 健, 上村 明男, 乾 誠
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Preparation of Novel Macrocyclic Compounds Deltaarenes2019

    • Author(s)
      Akio Kamimura, Ryusuke Watanabe, Takuji Kawamoto, and Michinori Sumimoto
    • Organizer
      18TH INTERNATIONAL SYMPOSIUM ON NOVEL AROMATIC COMPOUNDS (ISNA-18)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] A NEW MACROCYCLIC COMPOUND, DELTAARENES: PREPARATION AND DERIVATIZATION2019

    • Author(s)
      Akio Kamimura, Ryusuke Watanabe, Takuji Kawamoto
    • Organizer
      International Congress on Heteroatom Chemistry (ICHAC2019)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 2-スルファニルヒドロキノン二量体誘導体を用いたバイオイメージング材料開発の検討2019

    • Author(s)
      梅本春香, 本田健, 川本拓治, 上村明男
    • Organizer
      第46回有機典型元素化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Deltaarenes; Novel Sulfur-containing Macrocyclic Compounds2018

    • Author(s)
      Akio Kamimura,* Kazuki Ikeda and Takuji Kawamoto
    • Organizer
      The 15th International Symposium on Inorganic Ring Systems (IRIS15)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Chemical modification of a new macrocyclic molecule, deltaarene2018

    • Author(s)
      Kazuki Ikeda, Takuji Kawamoto, and Akio Kamimura
    • Organizer
      International Symposium on Main Group Chemistry Directed towards Organic Synthesis
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Deltaarenes, new macrocyclic compounds containing six sulfur atoms2018

    • Author(s)
      Akio Kamimura,* Ryusuke Watanabe, Kazuki Ikeda, and Takuji Kawamoto
    • Organizer
      The 28th International Symposium on the Organic Chemistry of Sulfur (ISOCS28)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of deltaarenes, Novel Macrocyclic Compounds2018

    • Author(s)
      Akio Kamimura,* Ryusuke Watanabe, Kazuki Ikeda, Takuji Kawamoto, and Michinori Sumimoto
    • Organizer
      The 13th International Symposium on Organic Reactions (ISOR13)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 2-スルファニルヒドロキノン二量体の光物性2017

    • Author(s)
      上村明男・坂本三四郎・松田貫太郎・川本拓治・隅本倫徳・星田尚司
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Ready switching of photoluminescence property of 2-sulfanylhydroquinone derivatives2017

    • Author(s)
      Tomoki Fukumitsu, Sanshiro Sakamoto, Michinori Sumimoto, Takuji Kawamoto, and Akio Kamimura
    • Organizer
      ISONIS11
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 2-スルファニルヒドロキノン二量体を用いた新規蛍光材料の開発2017

    • Author(s)
      福光智紀・坂本三四郎・隅本倫徳・川本拓治・上村明男
    • Organizer
      第44回有機典型元素化学討論会
    • Related Report
      2017 Annual Research Report
  • [Remarks] 独自に開発した青色蛍光染料を使ったバイオイメージング材料の開発に成功

    • URL

      http://www.chem.yamaguchi-u.ac.jp/research-achievement.html

    • Related Report
      2020 Annual Research Report

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Published: 2017-04-28   Modified: 2023-01-30  

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