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Realization of ultra-fast (fs) intersystem crossing of purely organic systems utilizing pai-radical substituent and elucidation of the mechanism

Research Project

Project/Area Number 18K19062
Research Category

Grant-in-Aid for Challenging Research (Exploratory)

Allocation TypeMulti-year Fund
Review Section Medium-sized Section 32:Physical chemistry, functional solid state chemistry, and related fields
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)

Project Period (FY) 2018-06-29 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥6,370,000 (Direct Cost: ¥4,900,000、Indirect Cost: ¥1,470,000)
Fiscal Year 2020: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2019: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Fiscal Year 2018: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsπラジカル / 超高速系間交差 / ペンタセン / π共役 / 増強系間交差 / 光耐久性 / 有機半導体 / フェムト秒系間交差 / 過渡吸収 / ペンタセン-ラジカル連結系 / 励起状態ダイナミクス / πトポロジー / ペンタセン誘導体 / 超高速過渡吸収 / 系間交差 / 励起二重項 / 励起四重項 / 超高速失活機構
Outline of Final Research Achievements

To establish the method to stabilize the unstable materials for the visible light without major modification of the electronic structures, we synthesized novel pentacene derivatives with both π-radical- and TIPS-substituents and their excited-state dynamics were evaluated. The pentacene-radical-linked systems showed a remarkable improvement in photochemical stability, which was more one-hundred times higher than that of 6,13-bis(triisopropylsilylethynyl)pentacene, which is a famous commercially available photostable pentacene derivative. Transient absorption spectroscopy showed that this remarkable photostability is due to the ultrafast intersystem crossing induced by effective π-conjugation between the radical substituent and pentacene moiety. The realization of the ultrafast intersystem crossing occurred within sub-pico second in the purely organic systems is the result with a potential to change the common sense of the excited-state dynamics of the organic materials.

Academic Significance and Societal Importance of the Research Achievements

ペンタセンは有機半導体の代表的な物質である。ペンタセン骨格とπラジカル部位とを強くπ共役させることにより、光耐久性の著しく高いペンタセン誘導体の代表格として知られているTIPS-ペンタセンを遥かに凌駕する光耐久性が実現できた点は、この種の手法を用いて光に不安定な物質を著しく安定化できる手法を示したことになり、その社会的意義は高い。また、重原子を含まない純有機化合物で、サブピコ秒程度(フェムト秒領域)で起こる系間交差を実現できることを示した点は、学術的意義が高いと判断される。

Report

(5 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Research-status Report
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (18 results)

All 2022 2021 2020 2019 2018

All Journal Article (2 results) (of which Peer Reviewed: 2 results,  Open Access: 2 results) Presentation (16 results) (of which Int'l Joint Research: 6 results,  Invited: 3 results)

  • [Journal Article] π-Topology and ultrafast excited-state dynamics of remarkably photochemically stabilized pentacene derivatives with radical substituents2022

    • Author(s)
      Nishiki Minami, Kohei Yoshida, Keijiro Maeguchi, Ken Kato, Akihiro Shimizu, Genta Kashima, Masazumi Fujiwara, Chiasa Uragami, Hideki Hashimoto, Yoshio Teki
    • Journal Title

      Physical Chemistry Chemical Physics

      Volume: 24 Issue: 22 Pages: 13514-13518

    • DOI

      10.1039/d2cp00683a

    • URL

      https://ocu-omu.repo.nii.ac.jp/records/2020390

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Photogenerated carrier dynamics of TIPSpentacene films as studied by photocurrent and electrically detected magnetic resonance2021

    • Author(s)
      Ken Kato, Yoshio Teki
    • Journal Title

      Physical Chemistry Chemical Physics

      Volume: 23 Issue: 11 Pages: 6351-6369

    • DOI

      10.1039/d0cp05125j

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] Excited-state spin alignment and spin dynamics of stable π-radicals2021

    • Author(s)
      Yoshio Teki
    • Organizer
      The 7th Kanto Aria Spin Chemisty Meeting
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] π-Topology and Ultra-Fast Excited-State Dynamics of Remarkably Photo-stabilized Pentacene Derivative Utilizing Radical Substituents2021

    • Author(s)
      Yoshio Teki, Keijiro Maeguchi, Nishiki Minami, Kohei Yoshida, Ken Kato, Akihiro Shimizu, Genta Kashima, Masazumi Fujiwara, Chiasa Uragami, Hideki Hashimoto
    • Organizer
      The 17th International Conference on Molecule-based Magnets
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research
  • [Presentation] πスピン系の励起状態ダイナミクスと磁気科学2021

    • Author(s)
      手木芳男
    • Organizer
      日本磁気科学会 令和3(2021)年 物理化学分科会
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] 平面安定ラジカルを2つ持つ新規ペンタセン誘導体の設計・合成とその光耐久性2021

    • Author(s)
      島田 幹太,吉田 考平, 手木 芳男
    • Organizer
      分子科学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] πトポロジーを考慮して励起スピン状態を制御した新規ペンタセン-ラジカル連結系の合成とその光耐久性2021

    • Author(s)
      南錦,前口慶治郎,加藤賢,吉田考平,清水章皓,加島源太,手木芳男
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Research-status Report
  • [Presentation] Study of Photo-Carrier Generation Dynamics in TIPS-Pentacene Film by Temperature Dependence of Electrically Detected Magnetic Resonance Measurements2021

    • Author(s)
      Ken Kato and Yoshio Teki
    • Organizer
      IES Virtual EPR Meeting
    • Related Report
      2020 Research-status Report
    • Int'l Joint Research
  • [Presentation] πトポロジーを利用して励起スピン状態を制御した新規ペンタセン ラジカルの合成とその基礎物性2020

    • Author(s)
      南錦, 前口慶治郎, 加藤賢, 吉田考平, 清水章皓, 加島源太, 手木芳男
    • Organizer
      第59回電子スピンサイエンス学会年会
    • Related Report
      2020 Research-status Report
  • [Presentation] 安定ラジカルを連結したペンタセン誘導体の合成と性質2020

    • Author(s)
      吉田考平・南 錦・手木芳男
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] Photocurrent and Electrically Detected Magnetic Resonance Study of Photo-Stable Pentacene derivatives2020

    • Author(s)
      Ken Kato, Akihiro Shimizu, Yoshio Teki
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] Photostable non-luminescent pentacene-radical derivative and luminescent radical excimer: Counters in unique excited-state spin dynamics of π-radicals2019

    • Author(s)
      Yoshio Teki
    • Organizer
      Spin Chemistry Meeting 2019
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Photocurrent Behaviour and Electrically Detected Magnetic Resonance Study of TIPS-Pentacene and Pentacene-Radical Derivative2019

    • Author(s)
      Ken Kato, Akihiro Shimizu, Yoshio Teki
    • Organizer
      Spin Chemistry Meeting 2019
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] ペンタセン誘導体の電気的検出磁気共鳴(EDMR)測定2019

    • Author(s)
      加藤賢, 清水章皓, 手木芳男
    • Organizer
      第13回分子科学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] TIPS基とラジカル置換基を有するペンタセン誘導体の設計・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
      第13回分子科学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] TIPS-ペンタセンおよびペンタセンラジカル誘導体の光電流挙動と電気的検出磁気共鳴測定2019

    • Author(s)
      加藤賢, 清水章皓, 手木芳男
    • Organizer
      第58回電子スピンサイエンス学会年会
    • Related Report
      2019 Research-status Report
  • [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 Research-status Report
  • [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 Research-status Report
    • Int'l Joint Research

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Published: 2018-07-25   Modified: 2023-01-30  

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