Development of Organic Active Materials for Redox-Flow Batteries

• Project/Area Number: 25410200
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Energy-related chemistry
• Research Institution: Kyoto University
• Principal Investigator: SHIMIZU AKIHIRO 京都大学, 工学(系)研究科(研究院), 助教 (30584263)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Project Status: Completed (Fiscal Year 2015)
• Budget Amount: ¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000); Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000); Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
• Keywords: レドックス・フロー電池 / 二次電池 / 再生可能エネルギー / 酸化還元 / 有機活物質 / 電解酸化

Outline of Final Research Achievements

To develop organic redox-flow batteries with high energy density, we designed and synthesized quinone materials with high solubility toward organic solvents. The nonaqueous redox-flow batteries using the materials showed higher energy densities than conventional aqueous redox-flow batteries.
We have also developed new electrochemical methods for alkene difunctionalization using halogen cations and for C-H amination of aromatic compounds via radical cations.

Research Products

• [Journal Article] Generation, Characterization, and Reactions of Thionium Ions Based on the Indirect Cation Pool Method (2016)
  • Author(s): Akihiro Shimizu, Keiji Takeda, Shota Mishima, Kodai Saito, Songhee Kim, Toshiki Nokami, Jun-ichi Yoshida*
  • Journal Title: Bull. Chem. Soc. Jpn. Volume: 89 Issue: 1 Pages: 61-66
  • DOI: 10.1246/bcsj.20150323
  • NAID: 130005119459
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Heterocyclization Approach for Electrooxidative Coupling of Functional Primary Alkylamines with Aromatics (2015)
  • Author(s): Tatsuya Morofuji, Akihiro Shimizu, Jun-ichi Yoshida
  • Journal Title: Journal of American Chemical Society Volume: 137 Issue: 31 Pages: 9816-9819
  • DOI: 10.1021/jacs.5b06526
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Reaction Integration Using Electrogenerated Cationic Intermediates (2015)
  • Author(s): J. Yoshida, A. Shimizu, Y. Ashikari, T. Morofuji, R. Hayashi, T. Nokami, A. Nagaki
  • Journal Title: Bulletin of the Chemical Society of Japan Volume: 88 Issue: 6 Pages: 763-775
  • DOI: 10.1246/bcsj.20150100
  • NAID: 130005075675
  • ISSN: 0009-2673, 1348-0634
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Electrochemical Intramolecular C-H Amination: Synthesis of Benzoxazoles and Benzothiazoles (2015)
  • Author(s): 諸藤達也、清水章弘、吉田潤一
  • Journal Title: Chemistry European Journal Volume: 21 Issue: 8 Pages: 3211-3214
  • DOI: 10.1002/chem.201406398
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Switching the Reaction Pathways of Electrochemically Generated β - Haloalkoxysulfonium Ions. Synthesis of Halohydrins and Epoxides (2015)
  • Author(s): Akihiro Shimizu , Ryutaro Hayashi, Yosuke Ashikari, Toshiki Nokami, Jun - ichi Yoshida*
  • Journal Title: Beilstein J. Org. Chem. Volume: 11 Pages: 242-248
  • DOI: 10.3762/bjoc.11.27
  • Peer Reviewed
• [Journal Article] Automated Electrochemical Assembly of the Protected Potential TMG-chitotriomycin Precursor Based on Rational Optimization of the Carbohydrate Building Block. (2015)
  • Author(s): Nokami, T.; Isoda, Y.; Sasaki, N.; Takaiso, A.; Hayase, S.; Itoh, T.; Hayashi, R.; Shimizu, A.; Yoshida, J.
  • Journal Title: Organic Letters Volume: 17 Issue: 6 Pages: 1525-1528
  • DOI: 10.1021/acs.orglett.5b00406
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Redox Active Dendronized Polystyrenes Equipped with Peripheral Triarylamines (2014)
  • Author(s): 野上敏材、武者直樹、諸藤達也、武田圭司、宅見正浩、清水章弘、吉田潤一
  • Journal Title: Beilstein Journal of Organic Chemistry Volume: 10 Pages: 3079-3103
  • DOI: 10.3762/bjoc.10.326
  • NAID: 120005540401
  • Peer Reviewed / Open Access
• [Journal Article] Direct C-N Coupling of Imidazoles with Aromatic and Benzylic Compounds via Electrooxidative C-H Functionalization (2014)
  • Author(s): 諸藤達也・清水章弘・吉田潤一
  • Journal Title: Journal of American Chemical Society Volume: 136 Issue: 12 Pages: 4496-4499
  • DOI: 10.1021/ja501093m
  • Peer Reviewed
• [Journal Article] Automated Solution-Phase Synthesis of Oligosaccharides via Iterative electrochemical Assembly of Thioglycosides (2013)
  • Author(s): Nokami, T.; Hayashi, R.; Saigusa, Y.; Shimizu, A.; Liu, C.-Y.; Mong, K.-K. T.; Yoshida, J.
  • Journal Title: Org. Lett. Volume: 15 Issue: 17 Pages: 4520-4523
  • DOI: 10.1021/ol402034g
  • Peer Reviewed
• [Journal Article] Halogen and Chalcogen Cation Pools Stabilized by DMSO. Versatile Reagents for Alkene Difunctionalization (2013)
  • Author(s): Ashikari, Y.; Shimizu, A.; Nokami, T.; Yoshida, J.
  • Journal Title: J. Am. Chem. Soc. Volume: 135 Issue: 43 Pages: 16070-16073
  • DOI: 10.1021/ja4092648
  • Peer Reviewed
• [Presentation] 活性種の電子状態の制御に基づく電子移動反応と有機電池材料の開発 (2016)
  • Author(s): 清水 章弘
  • Organizer: 第40回有機電子移動化学討論会
  • Place of Presentation: 新潟大学、新潟
  • Year and Date: 2016-06-23
  • Invited
• [Presentation] キノンを基盤とする有機正極活物質の設計・合成と酸化還元特性 (2016)
  • Author(s): 清水章弘・谷澤秀弥・矢三勇介・稲富友・北條伸彦・鈴木拡哲・吉田潤一
  • Organizer: 第40回有機電子移動化学討論会
  • Place of Presentation: 新潟大学、新潟
  • Year and Date: 2016-06-23
• [Presentation] 有機電気化学的手法による芳香族化合物と官能基を有する第一級アミンとの (2016)
  • Author(s): 清水章弘，諸藤達也，吉田潤一
  • Organizer: 2016年 電気化学会第83回大会
  • Place of Presentation: 大阪大学、大阪
  • Year and Date: 2016-03-29
• [Presentation] Direct Observation and Reactivity of Thionium Ions Generated by Using the Indirect Cation Pool Method (2015)
  • Author(s): Akihiro Shimizu, Keiji Takeda, Kodai Saito, Songhee Kim, Toshiki Nokami, Jun-ichi Yoshida
  • Organizer: Pacifichem 2015
  • Place of Presentation: Honolulu, Hawaii, USA
  • Year and Date: 2015-12-15
  • Int'l Joint Research
• [Presentation] Observation and Characterization of Electrochemically Generated Thionium Ions (2015)
  • Author(s): Akihiro Shimizu, Keiji Takeda, Shota Mishima, Kodai Saito, Songhee Kim, Toshiki, Nokami, Jun-ichi Yoshida*
  • Organizer: IKCOC-13 (The 13th International Kyoto Conference on New Aspect of Organic Chemistry)
  • Place of Presentation: リーガロイヤルホテル京都、京都
  • Year and Date: 2015-11-09
  • Int'l Joint Research
• [Presentation] 低温電解酸化による含硫黄反応中間体の発生・蓄積と求核剤との反応 (2015)
  • Author(s): 清水章弘・堀内俊・林竜太朗・武田圭史・三島翔太・齊藤巧泰・金松希・野上敏
  • Organizer: 第２６回基礎有機化学討論会
  • Place of Presentation: 松山、愛媛
  • Year and Date: 2015-09-24
• [Presentation] 窒素原子を導入したキノン誘導体の電気化学特性 (2015)
  • Author(s): 清水章弘・矢三勇介・辻井豊・野上敏材・稲富友・北條伸彦・鈴木拡哲・吉田潤一
  • Organizer: 第39回有機電子移動化学討論会
  • Place of Presentation: 長崎大学、長崎
  • Year and Date: 2015-06-26
• [Presentation] o- and p-Quinones Containing Nitrogen Atoms as Cathode Materials for Lithium Batteries (2015)
  • Author(s): Akihiro Shimizu, Yutaka Tsujii, Hiroki Kuramoto, Toshiki Nokami, Yuu Inatomi, Nobuhiko Hojo, and Jun-ichi Yoshida*
  • Organizer: 227th ECS Meeting
  • Place of Presentation: Chicago, Illinois, USA
  • Year and Date: 2015-05-24
  • Int'l Joint Research
• [Presentation] 活性種の安定化に基づく有機電子移動化学 (2015)
  • Author(s): 清水章弘
  • Organizer: 文部科学省 私立大学戦略的研究基盤形成支援事業 太陽光促進のためのエネルギーベストミックス研究拠点 平成27年度 「第1回光エネルギーセミナー」
  • Place of Presentation: 近畿大学、大阪
  • Year and Date: 2015-05-09
  • Invited
• [Presentation] 電気化学的手法により発生させたチオニウムイオンのNMRによる観測と安定性の評価 (2015)
  • Author(s): 清水章弘、武田圭史、齊藤巧泰、金 松希、野上敏材、吉田潤一
  • Organizer: 日本化学会第95春季年会(2015)
  • Place of Presentation: 千葉県 日本大学
  • Year and Date: 2015-03-26
• [Presentation] Generation, Observation, and Reactions of Thionium Ions by Indirect Cation Pool Method (2014)
  • Author(s): Akihiro Shimizu, Keiji Takeda, Kodai Saito, Songhee Kim, Toshiki Nokami, and Jun-ichi Yoshida
  • Organizer: The Ninth International Symposium on Integrated Synthesis (ISIS-9)
  • Place of Presentation: Awaji Yumebutai International Conference Center, Awaji Island
  • Year and Date: 2014-11-15
• [Presentation] 量子化学計算を用いた二次電池有機正極材料の設計と開発 (2014)
  • Author(s): 清水章弘, 辻井 豊, 倉本拓樹, 野上敏材, 稲富 友, 北條伸彦, 鈴木拡哲, 吉田潤一
  • Organizer: 2014年電気化学秋季大会
  • Place of Presentation: 北海道大学高等教育推進機構
  • Year and Date: 2014-09-27
  • Invited
• [Presentation] Nitrogen-Containing Polycyclic Quinones as Cathode Materials for Lithium Batteries (2014)
  • Author(s): Akihiro Shimizu, Yutaka Tsujii, Hiroki Kuramoto, Toshiki Nokami, Yuu Inatomi, Nobuhiko Hojo, and Jun-ichi Yoshida
  • Organizer: Electrochemistry 2014
  • Place of Presentation: Johannes Gutenberg-Universität Mainz
  • Year and Date: 2014-09-22
• [Presentation] キノンを正極材料に用いる有機電池のサイクル特性の向上と高電圧化 (2014)
  • Author(s): 清水章弘・倉本拓樹・辻井豊・矢三勇介・野上敏材・稲富友・北條伸彦・鈴木拡哲・吉田潤一
  • Organizer: 第38回有機電子移動化学討論会
  • Place of Presentation: 岐阜薬科大学
  • Year and Date: 2014-06-27
• [Presentation] リチウムカルボキシ基を導入したキノン誘導体を正極活物質に用いた有機電池 (2014)
  • Author(s): ○清水章弘・倉本拓樹・辻井 豊・野上敏材・稲富 友・北條伸彦・鈴木拡哲・吉田潤一
  • Organizer: 電気化学会第81回大会
  • Place of Presentation: 大阪
• [Presentation] Design, Synthesis, and Electrochemical Properties of Cyclic 1,2-Diketones as Organic Cathode Materials for Lithium-ion Batteries (2013)
  • Author(s): ○Akihiro Shimizu, Toshiki Nokami, Takahiro Matsuo, Yuu Inatomi, Nobuhiko Hojo, Takafumi Tsukagoshi, Hiroshi Yoshizawa, Hiroki Kuramoto, and Jun-ichi Yoshida
  • Organizer: The 223rd ECS Meeting
  • Place of Presentation: トロント、カナダ
• [Presentation] 1,2-ジケトンを基本構造とするリチウムイオン二次電池正極用有機レドックスポリマーの開発 (2013)
  • Author(s): ○清水章弘・倉本拓樹・辻井 豊・野上敏材・吉田潤一
  • Organizer: 第62回高分子討論会
  • Place of Presentation: 石川
• [Presentation] Polymer-Bound Pyrene-4,5,9,10-tetraone as a Cathode Material for Lithium-Ion Batteries (2013)
  • Author(s): ○Akihiro Shimizu, Toshiki Nokami, Hiroki Kuramoto, Yutaka Tsujii, Jun-ichi Yoshida
  • Organizer: ISOR-11, 2013 International Symposium on Organic Reaction
  • Place of Presentation: 台北、台湾
• [Remarks] 京都大学大学院工学研究科 合成・生物化学専攻 吉田研究室
  • URL: http://www.sbchem.kyoto-u.ac.jp/yoshida-lab/
• [Remarks] 京都大学大学院工学研究科 合成・生物化学専攻 吉田研究室
  • URL: http://www.sbchem.kyoto-u.ac.jp/yoshida-lab/