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Basic study of pai-radicals toward spintronics devices utilizing excited-state dynamics

Research Project

Project/Area Number 16H04136
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Functional solid state chemistry
Research InstitutionOsaka City University

Principal Investigator

TEKI YOSHIO  大阪市立大学, 大学院理学研究科, 教授 (00180068)

Co-Investigator(Kenkyū-buntansha) 吉野 治一  大阪市立大学, 大学院理学研究科, 准教授 (60295681)
仕幸 英治  大阪市立大学, 大学院工学研究科, 教授 (90377440)
Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥17,940,000 (Direct Cost: ¥13,800,000、Indirect Cost: ¥4,140,000)
Fiscal Year 2018: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2017: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2016: ¥9,620,000 (Direct Cost: ¥7,400,000、Indirect Cost: ¥2,220,000)
Keywordsπラジカル / 励起状態ダイナミクス / ペンタセン誘導体 / 有機半導体材料 / スピン流 / 発光性ラジカル / エキシマー形成初期過程 / 分子スピントロニクス / 光電流 / 磁場効果 / 光検出ESR / 時間分解発光 / スピントロニクス / 薄膜素子 / 有機電荷移動錯体 / 励起状態ダイナミックス / スピン輸送 / 光励起状態 / 電荷移動錯体 / 時間分解ESR / 光耐久性 / ペンタセン
Outline of Final Research Achievements

Four representative results were obtained. (1) Pentacene derivatives having both radical- and triisopropylsilylethynyl (TIPS) substituent were synthesized. Remarkable photostability improvement ca. 50 times than that of 6,13-bis(triisopropylsilylethynyl)pentacene (TIPS-pentacene) was achieved. (2) The photoconductivity and magnetoconductance in the thin film of a typical weak charge-transfer complex (pyrene/dimethylpyromellitdiimide) was investigated and the excited-state dynamics was clarified in detail. (3) The spin transport was successfully detected in thermally-evaporated TIPS-pentacene films. (4) The excited-state dynamics of the photostable luminescent organic radical, (3,5-dichloro-4-pyridyl)bis(2,4,6-trichlorophenyl)methyl, doped in a host crystal was investigated by using optically detected ESR, time-resolved emission, and a quantum dynamics simulation. The initial process of excimer formation has been clarified for the first time from the viewpoint of the spin chemistry.

Academic Significance and Societal Importance of the Research Achievements

申請代表者らが見出した、ラジカル付加による光耐久性の向上方法を発展させることにより安定なペンタセン誘導体として市販もされているTIPS-ペンタセンを遥かに凌駕する光耐久性が実現できたことは、新規有機電子材料や有機半導体材料への展開を可能にする成果で、この種の系が実際に半導体材料として使用されることになれば、本研究成果の社会的意義と波及効果は極めて大きい。
また、発光性ラジカルの励起状態ダイナミクスの研究により、エキシマー形成の初期過程が初めてスピンをプローブとして用いることにより詳細に解明できた事は、ラジカルだけでなく分子の励起状態に対する新規な知見を与え、学術的意義の非常に高い成果である。

Report

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

    (37 results)

All 2019 2018 2017 2016

All Journal Article (4 results) (of which Peer Reviewed: 4 results,  Open Access: 1 results,  Acknowledgement Compliant: 1 results) Presentation (31 results) (of which Int'l Joint Research: 11 results,  Invited: 2 results) Book (1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Luminescent Radical-Excimer: Excited-State Dynamics of Luminescent Radicals in Doped Host Crystals2019

    • Author(s)
      Kato Ken、Kimura Shun、Kusamoto Tetsuro、Nishihara Hiroshi、Teki Yoshio
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 58 Issue: 9 Pages: 2606-2611

    • DOI

      10.1002/anie.201813479

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Spin transport in poly-acene films and the derivative films by using the spin-pumping2019

    • Author(s)
      Tanaka Yuji、Kono Taisei、Teki Yoshio、Shikoh Eiji
    • Journal Title

      IEEE Transactions on Magnetics

      Volume: 55 Issue: 2 Pages: 1400304

    • DOI

      10.1109/tmag.2018.2856275

    • NAID

      120006882173

    • URL

      https://ocu-omu.repo.nii.ac.jp/records/2019887

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photoconductivity and magnetoconductance effects on vacuum vapor deposition films of weak charge-transfer complexes2017

    • Author(s)
      Kato Ken、Hagi Shogo、Hinoshita Masumi、Shikoh Eiji、Teki Yoshio
    • Journal Title

      Physical Chemistry Chemical Physics

      Volume: 19 Issue: 29 Pages: 18845-18853

    • DOI

      10.1039/c7cp02781h

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Excited-state Dynamics and Spin-exchange Coupling of AnthraceneVerdazyl Radicalin Frozen Glass Matrix Investigated by Transient Absorption Spectroscopy2016

    • Author(s)
      A. Ito, M. Hinoshita, K. Kato and Y. Teki
    • Journal Title

      Chemistry Letters

      Volume: 45 Issue: 11 Pages: 1324-1326

    • DOI

      10.1246/cl.160697

    • NAID

      130005509453

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] TIPS 基とラジカル置換基の相乗効果による高い光耐久性を持つ有機ペンタセン-ラジカル誘導体の設計・合成とその物性2019

    • Author(s)
      前口 慶治郎, 加藤 賢, 清水 章皓, 加島 源太, 手木 芳男
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 光検出ESR と時間分解発光スペクトルによる発光性ラジカルの励起状態ダイナミクスの研究2019

    • Author(s)
      加藤 賢, 木村 舜, 草本 哲郎, 西原 寛, 手木 芳男
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Photocurrent behavior in polycrystalline film of pentacene-radical derivative2018

    • Author(s)
      Yoshio Teki, Akihiro Shimizu, Eiji Shikoh
    • Organizer
      The 12th International Conference on Excitonic and Photonic Processes in Condensed Matter and Nano Materials (EXCON2018)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] TRESR and EDMR study of excitonic and photocarrier processes in vacuum vapor deposition film of weak charge transfer complex2018

    • Author(s)
      Ken Kato, Shogo Hagi, Masumi Hinoshita, Eiji Shikoh, Yoshio Teki
    • Organizer
      The 12th International Conference on Excitonic and Photonic Processes in Condensed Matter and Nano Materials (EXCON2018)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Spin transport in poly-acene films and the derivative films by using the spin-pumping2018

    • Author(s)
      Yuji Tanaka, Taisei Kono, Yoshio Teki, Eiji. Shikoh
    • Organizer
      International Conference on Magnetism 2018 (ICM2018)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Photoconductivity and Magneto-Conductance Effect on Thin Films of Organic CT Complexes and Pentacene-Radical Derivative2018

    • Author(s)
      Yoshio Teki, Akihiro Shimizu, Ken Kato, Shogo Hagi, Masumi Hinoshita, Eiji Shikoh
    • Organizer
      43rd International Conference on Coordination Chemistry (ICCC2018)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Design, Syntheses and Photoconductivity of Pentacene-Radical Derivatives with Remarkable Photostability2018

    • Author(s)
      Yoshio Teki, Akihiro Shimizu, Ken Kato, Gennta Kashima, Eiji Shikoh
    • Organizer
      7th International Meeting on Spin in Organic Semiconductors (SpinOS 2018)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] TRESR and EDMR Study of Excitonic and Photocarrier Processes in Vacuum Vapor Deposition Film of Weak Charge Transfer Complex (II)2018

    • Author(s)
      Ken Kato, Shogo Hagi, Masumi Hinoshita, Eiji Shikoh, Yoshio Teki
    • Organizer
      7th International Meeting on Spin in Organic Semiconductors (SpinOS 2018)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 弱い電荷移動錯体蒸着膜のEDMR測定と光電流の低磁場効果2018

    • Author(s)
      萩彰吾, 加藤賢, 樋下万純, 仕幸英治, 手木芳男
    • Organizer
      第22回ESRフォーラム研究会
    • Related Report
      2018 Annual Research Report
  • [Presentation] π共役を伸ばしたアントラセン-ラジカル連結系の励起状態ダイナミクス (III)2018

    • Author(s)
      加藤 賢, 清水章皓, 手木 芳男
    • Organizer
      第22回ESRフォーラム研究会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 弱い電荷移動錯体の蒸着膜のEDMR測定と光電流の低磁場効果2018

    • Author(s)
      萩 彰吾, 加藤 賢, 樋下万純, 仕幸英治, 手木 芳男
    • Organizer
      第12回分子科学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] ODMR及び時間分解発光測定による発光性ラジカルの励起状態ダイナミクスの研究2018

    • Author(s)
      加藤賢, 木村舜. 草本哲郎, 西原寛, 手木芳男
    • Organizer
      第57回電子スピンサイエンス学会年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 弱い電荷移動錯体の蒸着膜における光電流の低磁場効果とTRESR及びEDMR測定2018

    • Author(s)
      萩彰吾,加藤賢, 樋下万純, 仕幸英治, 手木芳男
    • Organizer
      第57回電子スピンサイエンス学会年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Photoconductivity and magnetoconductance effect on vacuum vapor deposition films of weak charge-transfer complexes2017

    • Author(s)
      Yoshio Teki, Ken Kato, Shogo Hagi, Masumi Hinoshita, and Eiji Shikoh,
    • Organizer
      15th International Symposium on Spin and Magnetic Field Effects in Chemistry and Related Phenomena (SCM2017)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] スピンポンピングを用いたTIPSペンタセン蒸着膜のスピン輸送特性2017

    • Author(s)
      田中勇士、手木芳男、仕幸英治
    • Organizer
      第78回応用物理学会秋季学術講演会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ピレン-安定ラジカルの蒸着膜における光電流2017

    • Author(s)
      加藤 賢, 仕幸 英治, 手木 芳男
    • Organizer
      第11回分子科学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 弱い電荷移動錯体の蒸着膜における光電導性と磁場効果2017

    • Author(s)
      萩 彰吾, 加藤 賢, 樋下万純, 仕幸英治, 手木 芳男
    • Organizer
      第11回分子科学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 弱い電荷移動錯体の蒸着膜試料における光電流とその磁場効果2017

    • Author(s)
      加藤 賢, 萩 彰吾, 樋下 万純, 仕幸 英治, 手木 芳男
    • Organizer
      第7回CSJ化学フェスタ
    • Related Report
      2017 Annual Research Report
  • [Presentation] 光耐久性の高いペンタセン-ビラジカル誘導体の励起状態ダイナミクス2017

    • Author(s)
      清水 章皓、行平 奈央, 佐藤 大樹, 藤原 正澄, 橋本 秀樹, 手木 芳男
    • Organizer
      第7回CSJ化学フェスタ
    • Related Report
      2017 Annual Research Report
  • [Presentation] 弱い電荷移動錯体の蒸着膜における光電導性と磁場効果(Ⅱ)2017

    • Author(s)
      萩 彰吾, 加藤 賢, 樋下万純, 仕幸英治, 手木 芳男
    • Organizer
      第56回電子スピンサイエンス学会年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] π共役を伸ばしたアントラセン-ラジカル連結系の励起状態ダイナミクス(II)2017

    • Author(s)
      加藤 賢, 清水 章皓, 手木 芳男
    • Organizer
      8.第56回電子スピンサイエンス学会年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ペンタセン-ビラジカル誘導体の創成とその特異な光化学的性質を利用した著しい光耐久性の実現2016

    • Author(s)
      清水 章皓, 伊藤 亮孝, 手木 芳男
    • Organizer
      第6回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2016-11-14
    • Related Report
      2016 Annual Research Report
  • [Presentation] 有機πスピン系のスピン整列とスピン科学の解明2016

    • Author(s)
      手木芳男
    • Organizer
      第55回電子スピンサイエンス学会年会
    • Place of Presentation
      大阪市立大学(大阪府大阪市)
    • Year and Date
      2016-11-10
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 有機ラジカルを利用した高い光耐久性を有する新規ペンタセンの創成およびそのスピン物性2016

    • Author(s)
      清水 章皓, 伊藤 亮孝, 小澄 大輔, 橋本 秀樹, 手木 芳男
    • Organizer
      第55回電子スピンサイエンス学会年会
    • Place of Presentation
      大阪市立大学(大阪府大阪市)
    • Year and Date
      2016-11-10
    • Related Report
      2016 Annual Research Report
  • [Presentation] 平面性の高めたアントラセン-ラジカル化合物の合成および物性2016

    • Author(s)
      加藤賢, 清水章皓, 手木芳男
    • Organizer
      第55回電子スピンサイエンス学会年会
    • Place of Presentation
      大阪市立大学(大阪府大阪市)
    • Year and Date
      2016-11-10
    • Related Report
      2016 Annual Research Report
  • [Presentation] ニトロニルニトロキシドラジカル置換基を2つ有するペンタセン誘導体の光化学およびスピン物性2016

    • Author(s)
      清水 章皓, 伊藤 亮孝, 手木 芳男
    • Organizer
      第10回分子科学討論会
    • Place of Presentation
      神戸ファッションマート(兵庫県神戸市)
    • Year and Date
      2016-09-13
    • Related Report
      2016 Annual Research Report
  • [Presentation] Using Excited-State Spin-Dynamics of π-Radicals Toward Molecular Spintronics2016

    • Author(s)
      Y. Teki, A. Shimizu, Y. Kawanaka, A. Ito, D. Kosumi, and H. Hashimoto
    • Organizer
      The 15th International Conference on Molecule-Based Magnets
    • Place of Presentation
      仙台国際センター(宮城県仙台市)
    • Year and Date
      2016-09-04
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Photochmical Stability Enhancement of Pentacene Derivative Having Two Nitronyl Nitroxide Radical Substituents2016

    • Author(s)
      A. Shimizu, A. Ito and Y. Teki
    • Organizer
      The 15th International Conference on Molecule-Based Magnets
    • Place of Presentation
      仙台国際センター(宮城県仙台市)
    • Year and Date
      2016-09-04
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Photostabilization of Pentacene Derivatives Using Excited State Spin-Dynamics2016

    • Author(s)
      Y. Teki
    • Organizer
      The 20th Osaka City University International Workshop (OCUIC-2016) on Molecular Spins and Quantum Technology
    • Place of Presentation
      大阪市立大学(大阪府大阪市)
    • Year and Date
      2016-08-31
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and Physical Properties of Highly Coplanar π-Conjugated Anthracene-Radical Compound2016

    • Author(s)
      K. Kato, A. Shimizu, and Y. Teki
    • Organizer
      The 20th Osaka City University International Workshop (OCUIC-2016) on Molecular
    • Place of Presentation
      大阪市立大学(大阪府大阪市)
    • Year and Date
      2016-08-31
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ペンタセンと有機ラジカルの邂逅 ~著しい光耐久性の実現~2016

    • Author(s)
      清水 章皓, 伊藤 亮孝, 手木 芳男
    • Organizer
      化学人材育成プログラム 化学人材交流フォーラム2016
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Related Report
      2016 Annual Research Report
  • [Book] 電子スピサイエンス 15巻2017

    • Author(s)
      手木芳男
    • Total Pages
      10
    • Publisher
      電子スピサイエンス学会
    • Related Report
      2017 Annual Research Report
  • [Patent(Industrial Property Rights)] ペンタセンのラジカル誘導体およびその製造方法2018

    • Inventor(s)
      手木芳男、清水章皓、加島源大
    • Industrial Property Rights Holder
      公立大学法人大阪市立大学
    • Industrial Property Rights Type
      特許
    • Filing Date
      2018
    • Related Report
      2017 Annual Research Report

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Published: 2016-04-21   Modified: 2020-03-30  

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