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Synthesis of electron acceptors involving fluorine atoms and their application to organic cathod active materials

Research Project

Project/Area Number 24550213
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Functional materials/Devices
Research InstitutionOsaka Prefecture University

Principal Investigator

Matsubara Hiroshi  大阪府立大学, 理学(系)研究科(研究院), 准教授 (20239073)

Project Period (FY) 2012-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000)
Fiscal Year 2014: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2013: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2012: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Keywordsベンゾキノン / 酸化剤 / 有機二次電池 / 正極活物質 / 電子受容体 / 二次電池 / 立体効果 / フッ素系化合物 / 含フッ素化合物
Outline of Final Research Achievements

In this study, we developed novel powerful oxidisers and cathode active materials of organic secondary batteries utilizing electron-withdrawing effect of perfluoroalkyl groups. 1,4-Benzoquinone derivatives bearing perfluoroalkyl groups (fluorous benzoquinones) were prepared and employed in the deprotection of silyl ethers. In addition, the prepared fluorous benzoquinones were evaluated as cathode active materials in rechargeable batteries; the cells exhibited higher voltage (3 V) in their charge-discharge curves. The fluorous benzoquinones effectively worked as positive-electrode materials, with improved charge-discharge cycle performance in the cells due to the stability of the benzoquinones toward decomposition during cycling. Bromine-substituted benzoquinones revealed high stability in charge-discharge cycle performance. We also attempted benzoquinone dimers and trimers to improve stability in charge and discharge cycle performance of the cells.

Report

(5 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (39 results)

All 2016 2015 2014 2013 2012 Other

All Journal Article (12 results) (of which Peer Reviewed: 12 results,  Acknowledgement Compliant: 9 results,  Open Access: 3 results) Presentation (19 results) Book (2 results) Remarks (6 results)

  • [Journal Article] teric Effects on the Cyclability of Benzoquinone-type Organic Cathode Active Materials for Rechargeable Batteries2015

    • Author(s)
      Yokoji,T.; Kameyama, Y.; Sakaida, S.; Maruyama, N.; Satoh, M.; Matsubara, H.
    • Journal Title

      Chem. Lett.

      Volume: 44 Issue: 12 Pages: 1726-1728

    • DOI

      10.1246/cl.150836

    • NAID

      130005112545

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Phase-Vanishing Method with Acetylene Evolution and Its Utilization in Several Organic Syntheses2015

    • Author(s)
      Matake, R.; Niwa, Y.; Matsubara, H.
    • Journal Title

      Org. Lett.

      Volume: 17 Issue: 10 Pages: 2354-2357

    • DOI

      10.1021/acs.orglett.5b00827

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] An ab-inito and DFT Study of the Autoxidation of THF and THP2015

    • Author(s)
      Matsubara, H.; Suzuki, S.; Hirano, S.
    • Journal Title

      Org. Biomol. Chem.

      Volume: 13 Issue: 16 Pages: 4686-4692

    • DOI

      10.1039/c5ob00012b

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A Grignard-type Phase-vanishing Method: Generation of Organomagnesium Reagent and Its Subsequent Addition to Carbonyl Compounds2015

    • Author(s)
      Matsubara, H.; Niwa, Y.; Matake, R.
    • Journal Title

      Synlett

      Volume: 26 Issue: 09 Pages: 1276-1280

    • DOI

      10.1055/s-0034-1380381

    • NAID

      120005767783

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Rechargeable organic lithium-ion batteries using electron-deficient benzoquinones as positive-electrode materials with high discharge voltages2014

    • Author(s)
      Yokoji, T.; Matsubara, H.; Satoh, M.
    • Journal Title

      J. Mater. Chem. A

      Volume: 2 Issue: 45 Pages: 19347-19354

    • DOI

      10.1039/c4ta02812k

    • NAID

      120005767778

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and properties of fluorous benzoquinones and their application in deprotection of silyl ethers2014

    • Author(s)
      Matsubara, H.; Maegawa, T.; Kita, Y.; Yokoji, T.; Nomoto, A.
    • Journal Title

      Org. Biomol. Chem.

      Volume: 12 Issue: 29 Pages: 5442-5447

    • DOI

      10.1039/c4ob00783b

    • NAID

      120005767779

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Radical vinylation of dioxolanes and N-acylpyrrolidines using vinyl bromides2014

    • Author(s)
      Kippo, T.; Kimura, Y.; Maeda, A.; Matsubara, H.; Fukuyama, T.; Ryu, I.
    • Journal Title

      Org. Chem. Front.

      Volume: 1 Issue: 7 Pages: 755-758

    • DOI

      10.1039/c4qo00138a

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] A Theoretical Study for Reduction of Acyl Radicals with Borohydride Anions2014

    • Author(s)
      Kawamoto, T.; Matsubara, H.; Ryu, I.
    • Journal Title

      Chem. Lett.

      Volume: 43 Issue: 7 Pages: 1140-1142

    • DOI

      10.1246/cl.140370

    • NAID

      130004868283

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Borohydride-Mediated Radical Addition Reactions of Organic Iodides to Electron-Deficient Alkenes2014

    • Author(s)
      Kawamoto, T., Uehara, S. ; Hirao, H. ; Fukuyama, T. ; Matsubara, H. ; Ryu, I.
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 79 Issue: 9 Pages: 3999-4007

    • DOI

      10.1021/jo500464q

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Revisiting the bromination of C-H bonds with molecular bromine by using a photo-microflow system.2014

    • Author(s)
      Manabe, Y., Kitawaki, Y., Nagasaki, M., Fukase, K., Matsubara, H., Hino, Y., Fukuyama, T., Ryu, I.
    • Journal Title

      Chem. Eur. J.

      Volume: 20 Issue: 40 Pages: 12750-12753

    • DOI

      10.1002/chem.201402303

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Copper-Catalyzed Extended Pummerer Reactions of Ketene Dithioacetal Monoxides with Alkynyl Sulfides and Ynamides with an Accompanying Oxygen Rearrangement2013

    • Author(s)
      村上慧、井本潤一、松原浩、吉田優、依光英樹、大嶌罵幸一郎
    • Journal Title

      Chemistry -A European Journal

      Volume: (In press) Issue: 18 Pages: 5625-5630

    • DOI

      10.1002/chem.201204072

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Lactone Radical Cyclizations and Cyclization Cascades Mediated by SmI2-H2O2012

    • Author(s)
      Parmer, D.; Matsubara, H.; Price, K.; Spain, M.; Procter, D. J.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 134 Issue: 30 Pages: 12751-12757

    • DOI

      10.1021/ja3047975

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] フェイズ・バニシング法によるTiCl4を用いた有機合成2016

    • Author(s)
      足達裕介・松原 浩
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] カルシウムカーバイドを用いたビニルエーテル合成2016

    • Author(s)
      眞武亮介・足達裕介・松原 浩
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] HBr/1,4-dioxane溶液の調製とその利用2015

    • Author(s)
      西尾勇弥・ 御船亮太・松原 浩・佐藤泰輔・曽我真一
    • Organizer
      2015ハロゲン利用ミニシンポジウム(第8回臭素化学懇話会年会)
    • Place of Presentation
      島根大学(島根県松江市)
    • Year and Date
      2015-11-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] ベンゾキノン多量体のリチウムイオン二次電池用正極活物質への利用2015

    • Author(s)
      横地崇人・坂井田俊・丸山則彦・佐藤正春・松原 浩
    • Organizer
      第56回電池討論会
    • Place of Presentation
      愛知県産業労働センター(愛知県名古屋市)
    • Year and Date
      2015-11-11
    • Related Report
      2015 Annual Research Report
  • [Presentation] フェイズ・バニシング法を利用したチタニウムエノラートによるα,β-不飽和アルデヒドの合成2015

    • Author(s)
      足達裕介・松原 浩
    • Organizer
      フルオラス科学第8回シンポジウム
    • Place of Presentation
      清水テルサ(静岡県静岡市)
    • Year and Date
      2015-10-02
    • Related Report
      2015 Annual Research Report
  • [Presentation] ペルフルオロアルキル鎖を有する山口試薬の合成と反応性解析2015

    • Author(s)
      西尾勇弥・河津朱里・松原 浩
    • Organizer
      第38回フッ素化学討論会
    • Place of Presentation
      日本橋公会堂(東京都中央区)
    • Year and Date
      2015-09-17
    • Related Report
      2015 Annual Research Report
  • [Presentation] 二次電池用ベンゾキノン系有機正極活物質におけるサイクル特性の改善2015

    • Author(s)
      横地崇人・亀山侑季・坂井田 俊・丸山則彦・佐藤正春・松原 浩
    • 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(千葉県・船橋市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] ハロゲンを有するベンゾキノン系化合物の二次電池正極活物質への利用2014

    • Author(s)
      横地崇人・松原 浩
    • Organizer
      2014ハロゲン利用ミニシンポジウム(第7回臭素化学懇話会年会)
    • Place of Presentation
      日本大学 理工学部駿河台キャンパス(東京都・千代田区)
    • Year and Date
      2014-12-12
    • Related Report
      2014 Research-status Report
  • [Presentation] 2,2'-Bis-p-benzoquinone誘導体のリチウムイオン電池用正極活物質への利用,2014

    • Author(s)
      横地崇人・松原 浩・佐藤正春
    • Organizer
      第55回電池討論会
    • Place of Presentation
      国立京都国際会館(京都府・京都市)
    • Year and Date
      2014-11-19 – 2014-11-21
    • Related Report
      2014 Research-status Report
  • [Presentation] ペルフルオロカーボンを利用した気体の発生と有機合成への利用2014

    • Author(s)
      眞武亮介・丹羽勇樹・松原 浩,
    • Organizer
      第37回フッ素化学討論会
    • Place of Presentation
      大阪府立男女共同参画・青少年センター(ドーンセンター)(大阪府・大阪市)
    • Year and Date
      2014-10-30 – 2014-10-31
    • Related Report
      2014 Research-status Report
  • [Presentation] ハロゲンを有するベンゾキノン誘導体の二次電池への応用2014

    • Author(s)
      横地祟人, 松原 浩, 佐藤正春
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] ペルフルオロアルキル基を有する山口試薬の開発2014

    • Author(s)
      河津朱里, 松原 浩
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] フルオラスハイブリッド溶媒の開発と有機合成への利用2014

    • Author(s)
      葛原満広, 松原 浩
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] フッ素及びペルフルオロアルキル基を有するベンゾキノン類の合成と二次電池正極活物質への利用,2013

    • Author(s)
      横地祟人, 松原 浩
    • Organizer
      第36回フッ素化学討論会
    • Place of Presentation
      つくば
    • Related Report
      2013 Research-status Report
  • [Presentation] 電子求引性置換基を有するベンゾキノン誘導体の二次電池正極活物質への利用2013

    • Author(s)
      横地祟人, 松原 浩, 佐藤正春
    • Organizer
      第54回電池討論会, 大阪, 2013年10月.
    • Place of Presentation
      大阪
    • Related Report
      2013 Research-status Report
  • [Presentation] フルオラス山口試薬の合成とその利用2013

    • Author(s)
      河津朱里, 松原 浩
    • Organizer
      フルオラス科学第6回シンポジウム
    • Place of Presentation
      岡山
    • Related Report
      2013 Research-status Report
  • [Presentation] BTF系ハイブリッド溶媒の開発と有機合成への利用2013

    • Author(s)
      葛原満広, 松原 浩
    • Organizer
      フルオラス科学第6回シンポジウム
    • Place of Presentation
      岡山
    • Related Report
      2013 Research-status Report
  • [Presentation] ベンゾキノン誘導体の二次電池への応用2013

    • Author(s)
      横地崇人・松原 浩・佐藤正春
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・草津キャンパス
    • Related Report
      2012 Research-status Report
  • [Presentation] 新規フルオラスハイブリッド溶媒の合成とその性質2012

    • Author(s)
      葛原満広・松原 浩
    • Organizer
      フルオラス科学第5回シンポジウム
    • Place of Presentation
      仙台
    • Related Report
      2012 Research-status Report
  • [Book] フッ素系溶媒の特徴と有機合成2013

    • Author(s)
      松原 浩
    • Total Pages
      350
    • Publisher
      S&T出版
    • Related Report
      2012 Research-status Report
  • [Book] Fluorous Organic Hybride Solvents for Non-fluorous Organic Synthesis2012

    • Author(s)
      Matsubara, H.; Ryu
    • Total Pages
      411
    • Publisher
      Springer-Verlag
    • Related Report
      2012 Research-status Report
  • [Remarks] 研究概要

    • URL

      http://www.c.s.osakafu-u.ac.jp/~matsu/index.html

    • Related Report
      2015 Annual Research Report
  • [Remarks] 発表論文

    • URL

      http://www.c.s.osakafu-u.ac.jp/~matsu/papers.html

    • Related Report
      2015 Annual Research Report
  • [Remarks] 研究内容:ペルフルオロアルキル基の電子求引性の利用

    • URL

      http://www.c.s.osakafu-u.ac.jp/~matsu/research.html

    • Related Report
      2014 Research-status Report
  • [Remarks] 研究成果

    • URL

      http://www.c.s.osakafu-u.ac.jp/~matsu/papers.html

    • Related Report
      2014 Research-status Report
  • [Remarks] ペルフルオロアルキル基の電子求引性の利用

    • URL

      http://www.c.s.osakafu-u.ac.jp/̃matsu/research.html

    • Related Report
      2013 Research-status Report
  • [Remarks] ペルフルオロアルキル基の電子求引性の利用

    • URL

      http://www.c.s.osakafu-u.ac.jp/~matsu/research.html

    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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