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Synthesis and properties of pi-conjugation open-shell species featured by carbon tethers

Research Project

Project/Area Number 16H04106
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionKanagawa University

Principal Investigator

Tsuji Hayato  神奈川大学, 理学部, 教授 (20346050)

Project Period (FY) 2016-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥16,900,000 (Direct Cost: ¥13,000,000、Indirect Cost: ¥3,900,000)
Fiscal Year 2019: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Fiscal Year 2018: ¥3,380,000 (Direct Cost: ¥2,600,000、Indirect Cost: ¥780,000)
Fiscal Year 2017: ¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000)
Fiscal Year 2016: ¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Keywordsπ共役 / 構造制御 / フェニレンビニレン / 開殻系 / 光物性 / 電子物性 / 共鳴トンネル / 有機化学 / 開殻分子
Outline of Final Research Achievements

The evaluation of COPV derivatives using radical cations and dications showed that the charge delocalization effect of COPV is due to the ideal electron conjugation effect and that COPV is useful as an electronic wire. We also succeeded in synthesizing a double-decker COPV derivative to evaluate the electronic interaction through space. Furthermore, the usefulness of thermodynamically and kinetically stabilized derivatives for improving the stability of open-shell systems and excited states was confirmed from their synthesis and stability evaluation. Based on these basic research results ,the room-temperature resonance tunneling phenomenon was also observed in single molecule device applications.

Academic Significance and Societal Importance of the Research Achievements

従来では、極低温で分子構造を物理的に「凍結」させた状態でしか観測されなかった機能が、化学的に分子構造が理想的な形に固定されたCOPVでは、室温でも優れた機能性を発現することが一連の研究によって明らかとなった。これは、単分子ワイヤの研究成果によって顕著に示されており、従来のトランジスタを10分の1程度のサイズ、100~1000倍程度の高速化を室温で実現する可能性が拓けた。また誘導化によって、目的とする性質をより優先的に発現したり高い安定性を実現したりするなど、構造-機能相関という学術的な観点に加えて社会実装のための基礎的かつ重要な知見を得た。

Report

(5 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • Research Products

    (37 results)

All 2020 2019 2018 2017 2016 Other

All Int'l Joint Research (6 results) Journal Article (12 results) (of which Int'l Joint Research: 7 results,  Peer Reviewed: 12 results,  Open Access: 2 results,  Acknowledgement Compliant: 1 results) Presentation (17 results) (of which Int'l Joint Research: 7 results,  Invited: 5 results) Remarks (2 results)

  • [Int'l Joint Research] University of Alicante/University of Malaga(スペイン)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] FAU(ドイツ)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] University of Malaga/Universit of Alicante(スペイン)

    • Related Report
      2017 Annual Research Report
  • [Int'l Joint Research] Friedrich Alexander University(ドイツ)

    • Related Report
      2017 Annual Research Report
  • [Int'l Joint Research] University of Malaga/University of Alicante(スペイン)

    • Related Report
      2016 Annual Research Report
  • [Int'l Joint Research] FAU/University of Wurzburg(ドイツ)

    • Related Report
      2016 Annual Research Report
  • [Journal Article] Kinetically Protected Carbon-bridged Oligo(p-phenylenevinylene) Derivatives for Blue Color Amplified Spontaneous Emission2020

    • Author(s)
      V. Bonal, M. Morales-Vidal, P. G. Boj, J. M. Villalvilla, J. A. Quintana, N. Lin, S. Watanabe, H. Tsuji, E. Nakamura, M. A. Diaz-Garcia
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: - Issue: 6 Pages: 751-758

    • DOI

      10.1246/bcsj.20200042

    • NAID

      130007856025

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Single-crystalline Optical Microcavities from Luminescent Dendrimers2020

    • Author(s)
      K. Iwai, H. Yamagishi, C. Herzberger, Y. Sato, H. Tsuji, K. Albrecht, K. Yamamoto, F. Sasaki, H. Sato, A. Asaithambi, A. Lorke, Y. Yamamoto
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: - Issue: 31 Pages: 12674-12679

    • DOI

      10.1002/anie.202000712

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Carbon‐bridged Oligo(phenylenevinylene)s as Light‐harvesting Antenna for Porphyrins2019

    • Author(s)
      H. Tsuji, A. Ichimura. M. Kudo, J. Sukegawa, E. Nakamura
    • Journal Title

      Chem. Asian J.

      Volume: 14 Issue: 10 Pages: 1672-1675

    • DOI

      10.1002/asia.201801715

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Conformational Control and Photophysical Properties of Methylene-Tethered Bis[(naphthalene-2-yl)vinyl]benzenes2019

    • Author(s)
      S. Watanabe, K. Yamanishi, H. Tsuji
    • Journal Title

      ChemPhotoChem

      Volume: 3 Issue: 8 Pages: 605-608

    • DOI

      10.1002/cptc.201900145

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Carbon-Bridged Oligo(phenylenevinylene)s: A de novo Designed Flat, Rigid, and Stable pi-Conjugated System2019

    • Author(s)
      H. Tsuji, E. Nakamura
    • Journal Title

      Acc. Chem. Res.

      Volume: 52 Issue: 10 Pages: 2939-2949

    • DOI

      10.1021/acs.accounts.9b00369

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Coherent Resonant Electron Tunneling at 9 and 300 K through a 4.5 nm Long, Rigid, Planar Organic Molecular Wire2018

    • Author(s)
      O. Chun, K. Hashimoto, H. Tsuji, E. Nakamura, Y. Majima
    • Journal Title

      ACS Omega

      Volume: 3 Issue: 5 Pages: 5125-5130

    • DOI

      10.1021/acsomega.8b00559

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] π-Electronic Cocrystal Microcavities with Selective Vibronic-Mode Light Amplification: Toward Forster Resonance Energy Transfer Lasing2018

    • Author(s)
      Daichi Okada, Stefano Azzini, Hiroki Nishioka, Anna Ichimura, Hayato Tsuji, Eiichi Nakamura, Fumio Sasaki, Cyriaque Genet, Thomas W. Ebbesen, Yohei Yamamoto*
    • Journal Title

      Nano Lett.

      Volume: 18 Issue: 7 Pages: 4396-4402

    • DOI

      10.1021/acs.nanolett.8b01442

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Carbon-bridged (p-phenylenevinylene) polymer for high-performance solution-processed distributed feedback lasers2018

    • Author(s)
      M. Morales-Vidal, J. A. Quintana, J. M. Villalvilla, P. G. Boj, H. Nishioka, H. Tsuji, E. Nakamura, G. L. Whitworth, G. A. Turnbull, I. D. W. Samuel and M. A. Diaz-Garcia
    • Journal Title

      Adv. Opt. Mater.

      Volume: 5 Issue: 13 Pages: 1800069-1800069

    • DOI

      10.1002/adom.201800069

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] An Efficient and Color-tunable Solution-processed Organic Thin Film Laser with a Polymeric Top-layer Resonator2017

    • Author(s)
      J. A. Quintana, J. M. Villalvilla, M. Morales-Vidal, P. G. Boj, X. Zhu, N. Ruangsupapichat, H. Tsuji, E. Nakamura, M. A. Diaz-Garcia
    • Journal Title

      Adv. Opt. Mater.

      Volume: 0 Issue: 19 Pages: 1700238-1700238

    • DOI

      10.1002/adom.201700238

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Carbon-Bridged Phenylene-Vinylenes: On the Common Diradicaloid Origin of Their Photonic and Chemical Properties2017

    • Author(s)
      R. C. Gonzalez-Cano, S. di Motta, X. Zhu, J. T. Lopez Navarrete, H. Tsuji, E. Nakamura, F. Negri, J. Casado
    • Journal Title

      J. Phys. Chem. C

      Volume: 121 Issue: 41 Pages: 23141-23148

    • DOI

      10.1021/acs.jpcc.7b08011

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Bis(aminoaryl) Carbon-Bridged Oligo(phenylenevinylene)s Expand the Limits of Electronic Couplings2017

    • Author(s)
      Paula Mayorga Burrezo, Nai-Ti Lin, Koji Nakabayashi, Shin-ichi Ohkoshi, Eva M. Calzado, Pedro G. Boj, Maria A. Diaz Garcia, Carlos Franco, Concepcim Rovira, Jaume Veciana, Michael Moos, Christoph Lambert, Juan T. Lopez Navarrete, Hayato Tsuji, Eiichi Nakamura, Juan Casado
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 56 Issue: 11 Pages: 2898-2902

    • DOI

      10.1002/anie.201610921

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Three-Dimensionally Homoconjugated Carbon-Bridged Oligophenylenevinylene for Perovskite Solar Cells2016

    • Author(s)
      Qifan Yan, Yunlong Guo, Anna Ichimura, Hayato Tsuji, Eiichi Nakamura
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 138 Issue: 34 Pages: 10897-10904

    • DOI

      10.1021/jacs.6b04002

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Presentation] Highly luminescent and stable hydrocarbon molecules featured by intramolecular carbon-bridging structure in oligo(phenylenevinylene)2020

    • Author(s)
      H. Tsuji
    • Organizer
      Japanese-German Workshop “Aquatic Materials Made to Order”
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 炭素架橋オリゴフェニレンビニレンを用いた有機レーザー2019

    • Author(s)
      辻 勇人
    • Organizer
      光化学討論会
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Carbon-bridged Oligo(phenylenevinylene)s (COPVn) with High Photoluminescence Efficiency and their Application to Organic Laser2019

    • Author(s)
      H. Tsuji
    • Organizer
      π-EJ2019
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 炭素架橋オリゴフェニレンビニレンと有機レーザーへの応用2019

    • Author(s)
      辻 勇人
    • Organizer
      第11回有機「ものつくり」研究会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Synthesis and Photophysical Properties of Dibenzo-fused Carbon-Bridged Oligo(p-Phenylenevinylene)s2019

    • Author(s)
      Shoya Watanabe, Hayato Tsuji
    • Organizer
      18th International Symposium on Novel Aromatic Compounds
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ダブルデッカー型炭素架橋フェニレンビニレンの合成および物性2019

    • Author(s)
      蔀朗弘、佐藤雄治、辻勇人
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 炭素架橋を用いたビス[(ナフタレン-2-イル)ビニル]ベンゼン(BNVB)の立体配座制御2019

    • Author(s)
      渡邊尚也、辻勇人
    • Organizer
      第9回CSJ化学フェスタ2019
    • Related Report
      2019 Annual Research Report
  • [Presentation] ダブルデッカー型炭素架橋フェニレンビニレン二量体の合成および物性2019

    • Author(s)
      蔀朗弘、佐藤雄治、辻勇人
    • Organizer
      第9回CSJ化学フェスタ2019
    • Related Report
      2019 Annual Research Report
  • [Presentation] ジベンゾ縮環した炭素架橋オリゴフェニレンビニレンの合成およびその高い光安定性2019

    • Author(s)
      渡邊尚也、辻勇人
    • Organizer
      第29回日本MRS年次大会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Carbon-bridged Oligo(phenylenevinylene)s: "Frozen" Molecules at Ambient Temperature2018

    • Author(s)
      Hayato Tsuji
    • Organizer
      ICPAC Langkawi2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Long-range Coherent Resonant Tunneling through Rigid Planar Carbon-bridged Oligo(phenylenevinylene)2018

    • Author(s)
      Hayato Tsuji, Ouyang Chun, Kohei Hashimoto, Eiichi Nakamura, Yutaka Majima
    • Organizer
      IKCOC 14
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 炭素架橋オリゴパラフェニレンビニレン類縁体の三次非線形光学物性についての理論研究2017

    • Author(s)
      西垣 佑亮・松井 啓史・高椋 章太・岸亮平・辻 勇人・中野 雅由
    • Organizer
      第20回理論化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] New reactions for constructing unique molecular structures: rigid planar phenylenevinylenes and sterically congested hydrocarbons2017

    • Author(s)
      Hayato Tsuji
    • Organizer
      π-System Figuration German-Japanese Workshop Heidelberg
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis, Properties, and Applications of Rigid Planar Carbon-bridged Oligo(phenylenevinylene)s2017

    • Author(s)
      Hayato Tsuji
    • Organizer
      2017 Exchange Symposium for Kanagawa University-National Taiwan University
    • Place of Presentation
      National Taiwan University, Taipei
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Theoretical study on third-order nonlinear optical property of carbon-bridged oligo para-phenylenevinylene(COPV)2017

    • Author(s)
      西垣佑亮・松井啓史・辻勇人・中野雅由
    • Organizer
      福井謙一記念研究センターシンポジウム
    • Place of Presentation
      京都
    • Related Report
      2016 Annual Research Report
  • [Presentation] 炭素架橋オリゴパラフェニレンビニレン(COPV)の開殻性と三次非線形光学物性の理論研究2017

    • Author(s)
      西垣佑亮・松井啓史・辻勇人・中野雅由
    • Organizer
      日本化学会第97春年会
    • Place of Presentation
      慶應義塾大学,横浜
    • Related Report
      2016 Annual Research Report
  • [Presentation] 剛直平面π共役系を持つ炭素架橋フェニレンビニレンの物性と応用2016

    • Author(s)
      辻 勇人
    • Organizer
      第26回MRSJ年次大会
    • Place of Presentation
      横浜
    • Related Report
      2016 Annual Research Report
  • [Remarks] 2つの準位から同時にレーザー発振する有機結晶を開発

    • URL

      https://www.kanagawa-u.ac.jp/pressrelease/details_16981.html

    • Related Report
      2018 Annual Research Report
  • [Remarks] 分子ワイヤの長距離共鳴トンネル現象を室温で確認~分子共鳴トンネルトランジスタの実現に期待~

    • URL

      https://www.kanagawa-u.ac.jp/pressrelease/details_16799.html

    • Related Report
      2018 Annual Research Report

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Published: 2016-04-21   Modified: 2021-02-19  

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