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C-H Bond transformations for n-type semiconductors of functional fullerenes and fullerene segments

Research Project

Project/Area Number 25288043
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionTohoku University

Principal Investigator

JIN Tienan  東北大学, 原子分子材料科学高等研究機構, 准教授 (80431493)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥18,460,000 (Direct Cost: ¥14,200,000、Indirect Cost: ¥4,260,000)
Fiscal Year 2015: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2014: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2013: ¥7,800,000 (Direct Cost: ¥6,000,000、Indirect Cost: ¥1,800,000)
KeywordsC-H結合変換反応 / n型半導体 / 官能基化フラーレン / フラーレン部分骨格 / C-H結合活性化
Outline of Final Research Achievements

Bulk heterojunction solar cells, based on P3HT donor and the deuterated C60 acceptor, exhibited a higher photovoltaic performance as compared to the corresponding protonated C60 device. By using a new Mn-promoted C60-cycloadditon, the standard OPV acceptors, such as PCBM and ICBA, have been obtained in extraordinarily high yields. The Cu-catalyzed C-H amination of the monofunctionalized hydrofullerenes and Ni-catalyzed dibenzylation of C60 efficiently produced the monoamino- and dibenzyl-substituted 1,4-adducts, respectively. A novel Pd-catalyzed cascade crossover-annulation of o-alkynylarylhalides and diarylacetylenes has been developed for the synthesis of dibenzo[a,e]pentalenes. A novel Pd-catalyzed dual C-H activation of bis-biaryl alkynes produced important and useful products 9,9'BF derivatives in high yields. A novel FeCl3-mediated oxidative spirocyclization has been developed for construction of a new class of dispirolinked π-conjugated molecules.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Annual Research Report
  • 2013 Annual Research Report
  • Research Products

    (43 results)

All 2016 2015 2014 2013 Other

All Journal Article (14 results) (of which Peer Reviewed: 13 results,  Open Access: 1 results,  Acknowledgement Compliant: 1 results) Presentation (17 results) (of which Int'l Joint Research: 3 results,  Invited: 2 results) Book (2 results) Remarks (4 results) Patent(Industrial Property Rights) (6 results) (of which Overseas: 5 results)

  • [Journal Article] FeCl3-Mediated Oxidative Spirocyclization of Difluorenylidene Diarylethanes Leading to Dispiro[fluorene-9,5′-indeno[2,1-a]indene-10′,9′′-fluorene]s2016

    • Author(s)
      Jian Zhao, Zhanqiang Xu, Kazuaki Oniwa, Naoki Asao, Yoshinori Yamamoto, Tienan Jin
    • Journal Title

      Angewandte Chemie International Edition Angewandte Chemie International Edition

      Volume: 55 Issue: 1 Pages: 259-263

    • DOI

      10.1002/anie.201507794

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Manganese powder promoted highly efficient and selective synthesis of fullerene mono- and biscycloadducts at room temperature2015

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

      Sci. Rep.

      Volume: 5 Issue: 1 Pages: 13920-13920

    • DOI

      10.1038/srep13920

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Pd-catalyzed cascade cyclization of o-alkynylarylbromides with dialkylalkynes via consecutive carbopalladation2015

    • Author(s)
      Zhao, J.; Asao, N.; Yamamoto, Y.; Jin, T.
    • Journal Title

      Tetrahedron Lett.

      Volume: 56 Issue: 23 Pages: 3133-3136

    • DOI

      10.1016/j.tetlet.2014.12.023

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Triflic Acid Mediated Cascade Cyclization of Aryldiynes for the Synthesis of Indeno[1,2-c]chromenes: Application to Dye-Sensitized Solar Cells.2015

    • Author(s)
      Jiang, H.; Ferrara, G.; Zhang, X.; Oniwa, K.; Islam, A.; Han, L.; Sun, Y.-J.; Bao, M.; Asao, N.; Yamamoto, Y.; Jin, T.
    • Journal Title

      Chem. Eur. J.

      Volume: 21 Issue: 10 Pages: 4065-4070

    • DOI

      10.1002/chem.201405860

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [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] 遷移金属触媒を用いた官能基化フラーレンの新規合成法の開発2015

    • Author(s)
      金 鉄男
    • Journal Title

      有機合成化学協会誌

      Volume: 73 Pages: 241-253

    • NAID

      130005065811

    • Related Report
      2014 Annual Research Report
    • Acknowledgement Compliant
  • [Journal Article] Pd-Catalyzed Synthesis of 9,9'-Bifluorenylidene Derivatives via Dual C-H Activation of Bis-biaryl Alkynes2014

    • Author(s)
      Zhao, J.; Asao, N.; Yamamoto, Y.; Jin, T.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 136 Issue: 27 Pages: 9540-9543

    • DOI

      10.1021/ja503252k

    • 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] Rh(III)-Catalyzed Regioselective Functionalization of C-H Bonds of Naphthylcarbamates for Oxidative Annulation with Alkynes2014

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

      Org. Let.

      Volume: 16 Issue: 18 Pages: 4830-4833

    • DOI

      10.1021/ol502317c

    • 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
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Metal-Catalyzed Annulation Reactions for p-Conjugated Polycycles2014

    • Author(s)
      Jin, T.; Zhao, J.; Asao, N.; Yamamoto, Y.
    • Journal Title

      Chem. Eur. J.

      Volume: 20 Issue: 13 Pages: 3554-3576

    • DOI

      10.1002/chem.201304640

    • Related Report
      2013 Annual Research 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 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 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pd-Catalyzed Cascade Crossover Annulation of o-Alkynylarylhalides and Diarylacetylenes Leading to Dibenzo[a,e]pentalenes2013

    • Author(s)
      Zhao, J.; Oniwa, K.; Asao, N.; Yamamoto, Y.; Jin, T.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 135 Issue: 28 Pages: 10222-10225

    • DOI

      10.1021/ja403382d

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Presentation] Oxidative Aromatization of 9-([1,1'-Biphenyl]-2-ylmethylene)-9H-fluorenes for Construction of Dibenzo[g,p]chrysenes2016

    • Author(s)
      Zhanqiang Xu, Xuan Zhang, Naoki Asao, Yoshinori Yamamoto, Tienan Jin
    • 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] Thieno[3,2-a]carbazole-based Organic Dyes for Dye-sensitized Solar Cells2016

    • Author(s)
      Tienan Jin, Hua Jiang, Kazuaki Oniwa, Ashraful Islam, Jian Zhao, Liyuan Han, Naoki Asao, Yoshinori Yamamoto
    • Organizer
      The AIMR International Symposium 2015 (AMIS 2015)
    • Place of Presentation
      仙台国際センター(宮城県・仙台市)
    • Year and Date
      2016-02-22
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Pd-Catalyzed Dual C-H Activation of Bis-biaryl Alkynes and Biaryl Alkynes2015

    • Author(s)
      Tienan Jin, Jian Zhao, Naoki Asao, Yoshinori Yamamoto
    • Organizer
      2015 International Chemical Congress of Pacific Basin Societies (PACIFICHEM2015)
    • Place of Presentation
      Hawaii (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Pd-Catalyzed Dual C-H Activation of Bis-biaryl Alkynes and Biaryl Alkynes2015

    • Author(s)
      Tienan Jin, Jian Zhao, Naoki Asao, Yoshinori Yamamoto
    • Organizer
      The 13th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-13)
    • Place of Presentation
      Rihga Royal Hotel (京都府・京都市)
    • Year and Date
      2015-11-09
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] C-H結合切断を経る新規環化付加反応による縮合多環式π共役系の構築2015

    • Author(s)
      金鉄男
    • Organizer
      触媒学会有機金属研究会 第43回オルガノメタリックセミナー「新しい分子変換に挑戦する有機金属化学」
    • Place of Presentation
      東北大学(宮城県・仙台市)
    • Year and Date
      2015-10-30
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] FeCl3-Mediated oxidative spirocyclization of difluorenylidene diarylethanes leading to dispirofluorene-indeno[2,1-a]indene-fluorenes2015

    • Author(s)
      Tienan Jin, Jian Zhao, Lingyu Li, Kazuaki Oniwa, Naoki Asao, Yoshinori Yamamoto
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学(大阪府・吹田市)
    • Year and Date
      2015-09-07
    • Related Report
      2015 Annual Research Report
  • [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
    • Organizer
      The AIMR International Symposium 2014
    • Place of Presentation
      Sendai, Japan
    • Related Report
      2013 Annual Research 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 Annual Research 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 Annual Research 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 Annual Research 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 Annual Research Report
  • [Presentation] Pd-Catalyzed Cascade Crossover-Annulation of o-Alkynylarylhalides and Diarylacetylenes Leading to Dibenzo[a,e]pentalenes2013

    • Author(s)
      Tienan Jin, Jian Zhao, Kazuaki Oniwa, Naoki Asao, Yoshinori Yamamoto
    • Organizer
      60th Symposium on Organometallic Chemistry
    • Place of Presentation
      学習院大学,東京
    • Related Report
      2013 Annual Research Report
  • [Presentation] Pd-Catalyzed Cascade Crossover-Annulation of o-Alkynylarylhalides and Diarylacetylenes Leading to Dibenzo[a,e]pentalenes2013

    • Author(s)
      Tienan Jin, Jian Zhao, Kazuaki Oniwa, Naoki Asao, Yoshinori Yamamoto
    • Organizer
      The Sixteenth International Symposium on Relations between Homogeneous and Heterogeneous Catalysis (ISHHC-16)
    • Place of Presentation
      北海道大学,札幌
    • Related Report
      2013 Annual Research Report
  • [Book] ACS Symposium Series eBooks: Nanomaterials for Sustainable Energy2015

    • Author(s)
      Tienan Jin, Md. Akhtaruzzaman, Yoshinori Yamamoto
    • Total Pages
      287
    • Publisher
      ACS Publications
    • Related Report
      2015 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
    • Total Pages
      247
    • Publisher
      ㈱シーエムシー出版
    • Related Report
      2013 Annual Research Report
  • [Remarks] 研究室ホームページー

    • URL

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

    • Related Report
      2015 Annual Research Report
  • [Remarks] 山本研ホームページ

    • URL

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

    • Related Report
      2014 Annual Research Report
  • [Remarks] 浅尾研究室ホームページ

    • URL

      http://www.wpi-aimr.tohoku.ac.jp/asao_labo/publication%20list.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 Annual Research Report
  • [Patent(Industrial Property Rights)] Fullerene derivative and method for manufacturing a fullerene derivative2014

    • Inventor(s)
      金鉄男、他3名
    • Industrial Property Rights Holder
      金鉄男、他3名
    • Industrial Property Rights Type
      特許
    • Filing Date
      2014-09-08
    • Acquisition Date
      2016-01-19
    • Related Report
      2015 Annual Research Report
    • Overseas
  • [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、他3名
    • Industrial Property Rights Holder
      金鉄男、他3名
    • Industrial Property Rights Type
      特許
    • Filing Date
      2013-09-25
    • Acquisition Date
      2016-01-26
    • Related Report
      2015 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 Annual Research Report
    • Overseas

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Published: 2013-05-21   Modified: 2019-07-29  

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