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Deuterium isotope effect for high performance organic solar cells

Research Project

Project/Area Number 25620021
Research Category

Grant-in-Aid for Challenging Exploratory Research

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

Principal Investigator

YAMAMOTO Yoshinori  東北大学, 原子分子材料科学高等研究機構, 名誉教授 (60029519)

Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords重水素同位体効果 / 光電変換効率 / 官能基化フラーレン / 触媒的フラーレンの官能基化 / 電子アクセプタ材料
Outline of Final Research Achievements

Our research aimed to synthesis of a new series of deuterated functional fullerenes for high performance organic bulk-heterojunction (BHJ) solar cells along with to develop novel catalytic fullerene functionalization reactions. As a result, the use of mono-substituted deuterofullerenes as a new series of electron acceptors for BHJ solar cells improved the power conversion efficiency up to 4.16% which was higher than their protonated fullerene analogues and the standard PC61BM device under the same conditions. Moreover, we have developed various new transition-metal-catalyzed fullerene functionalizations, such as Co-catalyzed highly mono-selective fullerene cycloaddition, Cu-catalyzed C-H amination of hydrofullerenes and Ni-catalyzed direct dibenzylation of fullerene for synthesis of 1,4-difunctional fullerenes.

Report

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

    (25 results)

All 2015 2014 2013 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (10 results) (of which Invited: 2 results) Book (3 results) Remarks (2 results) Patent(Industrial Property Rights) (4 results) (of which Overseas: 3 results)

  • [Journal Article] Ni-Catalyzed direct 1,4-difunctionalization of [60]fullerene with benzyl bromides2015

    • Author(s)
      Si, W.; Zhang, X.; Asao, N.; Yamamoto, Y.; Jin, T.
    • Journal Title

      Chem. Commun.

      Volume: 51 Issue: 29 Pages: 6392-6394

    • DOI

      10.1039/c5cc01534k

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cu-Catalyzed C-H Amination of Hydrofullerenes Leading to 1,4-Difunctionalized Fullerenes2014

    • Author(s)
      Si, W.; Lu, S.; Bao, M.; Asao, N.; Yamamoto, Y.; Jin, T.
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 2 Pages: 620-623

    • DOI

      10.1021/ol403573r

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] NBS-promoted oxidation of fullerene monoradicals leading to regioselective 1,4-difunctional fullerenes2014

    • Author(s)
      Si, W.; Lu, S.; Asao, N.; Bao, M.; Yamamoto, Y.; Jin, T.
    • Journal Title

      Chem. Commun.

      Volume: 50 Issue: 99 Pages: 15730-15732

    • DOI

      10.1039/c4cc07780f

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Deuterium Isotope Effect on BHJ Solar Cells. Enhancement of Organic Photovoltaic Performances using Monobenzyl Substituted Deuteriofullerene Acceptors2013

    • Author(s)
      Shirong Lu, Tienan Jin, Takeshi Yasuda, Weili Si, Kazuaki Oniwa, Khalid A. Alamry, Samia A. Kosa, Abdullah Mohamed Asiri, Liyuan Han, Yoshinori Yamamoto
    • Journal Title

      Organic Letters

      Volume: 15 Issue: 22 Pages: 5674-5677

    • DOI

      10.1021/ol4026606

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Co-Catalyzed Radical Cycloaddition of [60]Fullerene with Active Dibromides: Selective Synthesis of Carbocycle-Fused Fullerene Monoadducts2013

    • Author(s)
      Shirong Lu, Weili Si, Ming Bao, Yoshinori Yamamoto, Tienan Jin
    • Journal Title

      Organic Letters

      Volume: 15 Issue: 15 Pages: 4030-4033

    • DOI

      10.1021/ol401876n

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Functional 2-benzyl-1,2-dihydro[60]fullerenes as acceptors for organic photovoltaics : facile synthesis and high photovoltaic performances2013

    • Author(s)
      Shirong Lu, Tienan Jin, Takeshi Yasuda, Ashraful Islam, Md. Akhtaruzzaman, Liyuan Han, Khalid A. Alamry, Samia A. Kosa, Abdullah Mohamed Asiri, Yoshinori Yamamoto
    • Journal Title

      Tetrahedron

      Volume: 69 Issue: 4 Pages: 1302-1306

    • DOI

      10.1016/j.tet.2012.11.099

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] π-Conjugated Polycycles and Heterocycles through C-H and X-H Activation across Alkynes2015

    • Author(s)
      Yoshinori Yamamoto
    • Organizer
      the 16th Florida Heterocyclic and Synthetic Conference
    • Place of Presentation
      アメリカ
    • Year and Date
      2015-03-01 – 2015-03-04
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Pyrene End-Capped Oligothiophenes for Organic Light-Emitting Field Effect Transistors2015

    • Author(s)
      Kazuaki Oniwa, Yuki Abe, Hiromasa Kikuchi, Hidekazu Shimotani, Katsumi Tanigaki, Naoki Asao, Yoshinori Yamamoto, Tienan Jin
    • Organizer
      The AIMR International Symposium 2015 (AMIS 2015)
    • Place of Presentation
      仙台
    • Year and Date
      2015-02-17 – 2015-02-19
    • Related Report
      2014 Annual Research Report
  • [Presentation] Pd-Catalyzed Synthesis of 9,9’-Bifluorenylidene Derivatives via Dual C-H Activation of Bis-biaryl Alkynes2014

    • Author(s)
      Tienan Jin, Jian Zhao, Naoki Asao, Yoshinori Yamamoto
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      福岡
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Annual Research Report
  • [Presentation] Cu-Catalyzed C-H Amination of Hydrofullerenes Leading to 1,4-Difunctionalized Fullerenes2014

    • Author(s)
      Tienan Jin, Weili Si, Shirong Lu, Naoki, Asao, Yoshinori Yamamoto
    • Organizer
      XXVI International Conference on Organometallic Chemistry (ICOMC 2014)
    • Place of Presentation
      札幌
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] Pd-Catalyzed Synthesis of 9,9’-Bifluorenylidene Derivatives via Dual C-H Activation of Bis-biaryl Alkynes2014

    • Author(s)
      Jian Zhao, Naoki Asao, Yoshinori Yamamoto, Tienan Jin
    • Organizer
      XXVI International Conference on Organometallic Chemistry (ICOMC 2014)
    • Place of Presentation
      札幌
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] Remarkable Deuterium Isotope Effect of Deuterofullerene Acceptors on Organic Photovoltaic Performances2014

    • Author(s)
      Tienan Jin, Shirong Lu, Takeshi Yasuda, Weili Si1, Kazuaki Oniwa, Liyuan Han, Naoki Asao, Yoshinori Yamamoto
    • Organizer
      The AIMR International Symposium 2014
    • Place of Presentation
      Sendai, Japan
    • Related Report
      2013 Research-status Report
  • [Presentation] Cu-Catalyzed C-H Amination of Hydrofullerenes Leading to 1,4-Difunctionalized Fullerenes2013

    • Author(s)
      Weili Si, Shirong Lu, Naoki Asao, Yoshinori Yamamoto, Tienan Jin
    • Organizer
      10th International Symposium on Carbanion Chemistry (ISCC-10)
    • Place of Presentation
      Kyoto, Japan
    • Related Report
      2013 Research-status Report
  • [Presentation] Cu-Catalyzed C-H Amination of Hydrofullerenes Leading to 1,4-Difunctionalized Fullerenes2013

    • Author(s)
      Tienan Jin, Weili Si, Shirong Lu, Naoki Asao, Yoshinori Yamamoto
    • Organizer
      The Eighth International Symposium on Integrated Synthesis (ISIS-8)
    • Place of Presentation
      Nara, Japan
    • Related Report
      2013 Research-status Report
  • [Presentation] 遷移金属触媒を用いた官能基化フラーレンの選択的合成2013

    • Author(s)
      金鉄男
    • Organizer
      第12回化学系薬学若手研究者セミナー
    • Place of Presentation
      東北大学薬学研究科,仙台
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] New Organic Functional Materials for Solar Cells2013

    • Author(s)
      Yoshinori Yamamoto, Tienan Jin, Asao Naoki
    • Organizer
      246th American Chemical Society national Meeting & Exposition
    • Place of Presentation
      Indianapolis, USA
    • Related Report
      2013 Research-status Report
  • [Book] The Chemistry of Organogold Compounds2014

    • Author(s)
      B. S. Takale, M. Bao, Y. Yamamoto
    • Publisher
      John Wiley & Sons, Ltd.
    • Related Report
      2014 Annual Research Report
  • [Book] Gold Catalysis, A Homogeneous Approach2014

    • Author(s)
      N. Asao, N. Hatakeyama, Y. Yamamoto
    • Publisher
      World Scientific, Imperial College Press
    • Related Report
      2014 Annual Research Report
  • [Book] フラーレン誘導体・内包技術の最前線2014

    • Author(s)
      金 鉄男,山本 嘉則
    • Publisher
      ㈱シーエムシー出版
    • Related Report
      2013 Research-status Report
  • [Remarks] 研究室ホームページ

    • URL

      http://www.wpi-aimr.tohoku.ac.jp/yamamoto/index.html

    • Related Report
      2014 Annual Research Report
  • [Remarks] 山本研究室

    • URL

      http://www.wpi-aimr.tohoku.ac.jp/~yamamoto/index.html

    • Related Report
      2013 Research-status Report
  • [Patent(Industrial Property Rights)] フラーレンの環化反応2014

    • Inventor(s)
      金鉄男,山本嘉則,司偉麗,五十嵐威史
    • Industrial Property Rights Holder
      金鉄男,山本嘉則,司偉麗,五十嵐威史
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2014-182133
    • Filing Date
      2014-09-08
    • Related Report
      2014 Annual Research Report
  • [Patent(Industrial Property Rights)] Fullerene derivative and method for manufacturing a fullerene derivative2014

    • Inventor(s)
      金鉄男,山本嘉則,司偉麗,五十嵐威史
    • Industrial Property Rights Holder
      金鉄男,山本嘉則,司偉麗,五十嵐威史
    • Industrial Property Rights Type
      特許
    • Filing Date
      2014-06-26
    • Related Report
      2014 Annual Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] Fullerene derivatives, method of manufacturing Fullerene derivatives and solar cell2013

    • Inventor(s)
      金鉄男,山本嘉則,司偉麗,五十嵐威史
    • Industrial Property Rights Holder
      金鉄男,山本嘉則,司偉麗,五十嵐威史
    • Industrial Property Rights Type
      特許
    • Filing Date
      2013-09-25
    • Acquisition Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] フラーレン誘導体、フラーレン誘導体の製造方法及び太陽電池2013

    • Inventor(s)
      金鉄男,山本嘉則,司偉麗,五十嵐威史
    • Industrial Property Rights Holder
      金鉄男,山本嘉則,司偉麗,五十嵐威史
    • Industrial Property Rights Type
      特許
    • Filing Date
      2013-09-25
    • Related Report
      2013 Research-status Report
    • Overseas

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

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