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Development and application of organic n-type dopant using novel lithium-containing fullerene

Research Project

Project/Area Number 17K04970
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Nanostructural chemistry
Research InstitutionTohoku University (2019)
The University of Tokyo (2017-2018)

Principal Investigator

Okada Hiroshi  東北大学, 理学研究科, 客員研究者 (70518258)

Co-Investigator(Kenkyū-buntansha) 松尾 豊  名古屋大学, 工学研究科, 教授 (00334243)
Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2019: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2018: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2017: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordsフラーレン / 内包フラーレン / 有機半導体 / ドーピング / 電荷移動錯体
Outline of Final Research Achievements

The properties of the Li@C60, which is consisted of lithium cation and anionic fullerene C60-, as dopant was investigated. We fabricated thin film of C60 containing Li@C60. In the film, by the electron doping from Li@C60 to C60 solid state, the controlling of Fermi level and career density was achieved. This result is first example of doping without disturbing the solid-state structure of organic semiconductor.

Academic Significance and Societal Importance of the Research Achievements

無機半導体では,その性質を微調整するために,別の原子を少量加える『ドーピング』と呼ばれる処理が一般的におこなれます.有機半導体でも同様の処理がおこなれますが,別の分子を取り込むために,固体構造がドーピング前後で全く異なってしまうという問題がありました.今回,フラーレンの籠状骨格内にリチウム原子を持つリチウム内包フラーレンを用いることで,固体構造を変化させずドーピングを行えることを示しました.

Report

(4 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • 2017 Research-status Report
  • Research Products

    (30 results)

All 2019 2018 2017 Other

All Int'l Joint Research (4 results) Journal Article (9 results) (of which Int'l Joint Research: 6 results,  Peer Reviewed: 9 results) Presentation (14 results) (of which Int'l Joint Research: 8 results,  Invited: 3 results) Book (1 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Int'l Joint Research] USTC(中国)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] Aalto University School of Science(フィンランド)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] Univ. of Science and Technology of China/Northeast Normal University(中国)

    • Related Report
      2018 Research-status Report
  • [Int'l Joint Research] Northeast Normal University(中国)

    • Related Report
      2017 Research-status Report
  • [Journal Article] Synthesis of Benzothieno[60]fullerenes Through Fullerenyl Cation Intermediate2019

    • Author(s)
      Yutaka Matsuo, Yun Yu, Xiao-Yu Yang, Hiroshi Ueno, Hiroshi Okada, Hiromasa Shibuya, Yeong Suk Choi, Yong Wan Jin
    • Journal Title

      J. Org. Chem.

      Volume: 84 Issue: 10 Pages: 6270-6277

    • DOI

      10.1021/acs.joc.9b00549

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Improved Solubility of Asymmetric Tetraethynylporphyrin Derivatives for Solution-processed Organic Solar Cells2019

    • Author(s)
      Keisuke Ogumi, Takafumi Nakagawa, Hiroshi Okada, Yutaka Matsuo
    • Journal Title

      Org. Electron.

      Volume: 71 Pages: 50-57

    • DOI

      10.1016/j.orgel.2019.04.036

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chemical reduction of Li+@C60 by decamethylferrocene to produce neutral Li+@C60・-2019

    • Author(s)
      H. Okada, H. Ueno, Y. Takabayashi, T. Nakagawa, M. Vrankic;, J. Arvanitidis, T. Kusamoto, K. Prassides, and Y. Matsuo
    • Journal Title

      Carbon

      Volume: 153 Pages: 467-471

    • DOI

      10.1016/j.carbon.2019.07.028

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Li@C60 endohedral fullerene as a supraatomic dopant for C60 electron-transporting layers promoting the efficiency of perovskite solar cells2019

    • Author(s)
      Hiroshi Ueno, Il Jeon, Hao-sheng Lin, Abhishek Thote, Takafumi Nakagawa, Hiroshi Okada, Seiichiro Izawa, Masahiro Hiramoto, Hirofumi Daiguji, Shigeo Maruyama, Yutaka Matsuo
    • Journal Title

      Chemical Communications

      Volume: 55 Issue: 79 Pages: 11837-11839

    • DOI

      10.1039/c9cc06120g

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Controlled Redox of Lithium-Ion Endohedral Fullerene for Efficient and Stable Metal Electrode-Free Perovskite Solar Cells2019

    • Author(s)
      Jeon Il、Shawky Ahmed、Lin Hao-Sheng、Seo Seungju、Okada Hiroshi、Lee Jin-Wook、Pal Amrita、Tan Shaun、Anisimov Anton、Kauppinen Esko I.、Yang Yang、Manzhos Sergei、Maruyama Shigeo、Matsuo Yutaka
    • Journal Title

      Journal of the American Chemical Society

      Volume: 141 Issue: 42 Pages: 16553-16558

    • DOI

      10.1021/jacs.9b06418

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Highly soluble C2v-symmetrical fullerene derivatives: efficient synthesis, characterization, and electrochemical study2019

    • Author(s)
      Yue Ma, Kouya Uchiyama, Hiroshi Ueno, Hiroshi Okada, Hiroshi Moriyama, Yutaka Matsuo
    • Journal Title

      Org. Chem. Front.

      Volume: 印刷中 Issue: 9 Pages: 1372-1377

    • DOI

      10.1039/c9qo00056a

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Lithium-Ion Endohedral Fullerene (Li+@C60) Dopant in Stable Perovskite Solar Cells Inducing Anti-Oxidation2018

    • Author(s)
      Il Jeon, Hiroshi Ueno, Seungju Seo, Kerttu Aitola, Ryosuke Nishikubo, Akinori Saeki, Hiroshi Okada, Gerrit Boschloo, Shigeo Maruyama, Yutaka Matsuo
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 57 Issue: 17 Pages: 4607-4611

    • DOI

      10.1002/anie.201800816

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Crystallographic Structure Determination of Both [5,6]- and [6,6]-Isomers of Lithium-ion-containing Dipheylmethano[60]fullerene2017

    • Author(s)
      Hiroshi Okada, Hiroki Kawakami, Shinobu Aoyagi, Yutaka Matsuo
    • Journal Title

      J. Org. Chem.

      Volume: 82 Issue: 11 Pages: 5868-5872

    • DOI

      10.1021/acs.joc.7b00730

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Crystal Structure of Li+@Fluoreno[60]fullerene: Effect of Encapsulated Lithium Ion on Electrochemistry of Spiroannelated Fullerene2017

    • Author(s)
      Hiroshi Ueno, Hiroshi Okada, Shinobu Aoyagi, Yutaka Matsuo
    • Journal Title

      J. Org. Chem.

      Volume: 82 Issue: 21 Pages: 11631-11635

    • DOI

      10.1021/acs.joc.7b01893

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Presentation] Installing Various Functional Groups on Li+@C60 Using Azide-containing 1,3-Cyclohexadienes2019

    • Author(s)
      Hiroshi Okada, Takumi Takada, Shota Nagasawa, Yusuke Sasano, Eunsang Kwon, Yutaka Matsuo, Yoshiharu Iwabuchi
    • Organizer
      The 56th Fullerenes-Nanotubes-Graphene General Symposium
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] リチウムイオン内包フラーレンと有機小分子の簡便連結法の開発2019

    • Author(s)
      高田 拓実,長澤 翔太,笹野 裕介,岡田 洋史,權 垠相,松尾 豊,岩渕 好治
    • Organizer
      日本薬学会 第139年会
    • Related Report
      2018 Research-status Report
  • [Presentation] Basic Physico-Chemical Properties of C 2V-Symmetrical Octasubstituted Fullerene 52 Derivatives2018

    • Author(s)
      Yue Ma, Hiroshi Ueno, Hiroshi Okada, Kouya Uchiyama, Hiroshi Moriyama, Yutaka Matsuo
    • Organizer
      The 55th Fullerenes-Nanotubes-Graphene General Symposium
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Introduction of Methano Groups on Endhedral C60 Complex with Lithium2018

    • Author(s)
      H. Okada, H. Ueno, S. Aoyagi, Y. Matsuo
    • Organizer
      ICCC2018 Sendai Japan 43rd International Conference on Coordination Chemistry
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Highly Stabilized Perovskite Solar Cells by Li-Ion-Containing Fullerene Salt as Both Dopant and Anti-Oxidant2018

    • Author(s)
      Yutaka Matsuo, Il Jeon, Hiroshi Ueno
    • Organizer
      233rd Electrochemical Society (ECS) Meeting
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Endohedral lithium-ion-containing fullerene bearing diphenylmethano or fluoreno groups2018

    • Author(s)
      Hiroshi Okada, Hiroshi Ueno, Hiroki Kawakami, Shinobu Aoyagi, Yutaka Matsuo
    • Organizer
      The 98th CSJ Annual Meeting
    • Related Report
      2017 Research-status Report
  • [Presentation] Chemical Reduction of Lithium-ion-encapsulated Fullerene2018

    • Author(s)
      Hiroshi Okada, Hiroshi Ueno, Yasuhiro Takabayashi, Takeshi Nakagawa, Martina Vrankic, Shinobu Aoyagi, Ken Kokubo, Kimio Akiyama, Kosmas Prassides, Yutaka Matsuo
    • Organizer
      第54回 フラーレン・ナノチューブ・グラフェン総合シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] Highly Stabilized Perovskite Solar Cells by Li+-Encapsulated [60]Fullerene as Both Dopant and Anti-Oxidant2018

    • Author(s)
      Hiroshi Ueno, Il Jeon, Seungju Seo, Ryosuke Nishikubo, Hiroshi Okada, Akinori Saeki, Shigeo Maruyama, Yutaka Matsuo
    • Organizer
      第54回 フラーレン・ナノチューブ・グラフェン総合シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] High Stability Perovskite Solar Cells by Li+-Containing Fullerene Salt as both Dopant and Anti-Oxidant2018

    • Author(s)
      Hiroshi Ueno, Il Jeon, Seungju Seo, Shigeo Maruyama, Yutaka Matsuo
    • Organizer
      The 98th CSJ Annual Meeting
    • Related Report
      2017 Research-status Report
  • [Presentation] Derivatization of Lithium-ion-containing fullerene, Li+@C602017

    • Author(s)
      Hiroshi Okada, Hiroki Kawakami, Yutaka Matsuo
    • Organizer
      2nd International Symposium of NanoCarbons
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis, Characterization and Electrochemistry of Lithium Ion-Encapsulated Fluoreno[60]Fullerene2017

    • Author(s)
      Hiroshi Ueno, Hiroshi Okada, Shinobu Aoyagi, Yutaka Matsuo
    • Organizer
      第53回 フラーレン・ナノチューブ・グラフェン総合シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] High Stability Perovskite Solar Cells by Li+-Containing Fullerene Salt as both Dopant and Anti-Oxidant2017

    • Author(s)
      Hiroshi Ueno, Il Jeon, Seungju Seo, Shigeo Maruyama, Yutaka Matsuo
    • Organizer
      2017MRS fall meeting
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Modification of Lithium-Ion-Containing [60]Fullerene: Synthesis and Successful Preparation of Both [5,6]- and [6,6]-Isomers2017

    • Author(s)
      Yutaka Matsuo, Hiroshi Okada, Hiroshi Ueno, Shinobu Aoyagi
    • Organizer
      231st Electrochemical Society (ECS) Meeting
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Chemical Modification of Lithium-ion-containing [60]Fullerene: Synthesis and Structural Characterization of Both [5,6]- and [6,6]-Methano[60]fullerene2017

    • Author(s)
      Yutaka Matsuo
    • Organizer
      2nd International Symposium on NanoCarbon (ISNC2017)
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Book] Endohedral Lithium-containing Fullerenes Preparation, Derivatization, and Application2017

    • Author(s)
      Matsuo, Yutaka, Okada, Hiroshi, Ueno, Hiroshi
    • Total Pages
      140
    • Publisher
      Springer Singapore
    • ISBN
      9789811050039
    • Related Report
      2017 Research-status Report
  • [Remarks] Matsuo Group at USTC and Tokyo

    • URL

      http://www.matsuo-lab.net

    • Related Report
      2017 Research-status Report
  • [Patent(Industrial Property Rights)] n型有機半導体層、有機半導体装置及びn型ドーパント2019

    • Inventor(s)
      松尾 豊,上野 裕,田 日,岡田 洋史
    • Industrial Property Rights Holder
      松尾 豊,上野 裕,田 日,岡田 洋史
    • Industrial Property Rights Type
      特許
    • Filing Date
      2019
    • Related Report
      2019 Annual Research Report

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Published: 2017-04-28   Modified: 2021-02-19  

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