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Pi-Figuration of Functional Molecules based on Flexible Conformational Change

Publicly Offered Research

Project Areapi-System Figuration: Control of Electron and Structural Dynamism for Innovative Functions
Project/Area Number 17H05155
Research Category

Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionOsaka University

Principal Investigator

武田 洋平  大阪大学, 工学研究科, 准教授 (60608785)

Project Period (FY) 2017-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥7,280,000 (Direct Cost: ¥5,600,000、Indirect Cost: ¥1,680,000)
Fiscal Year 2018: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2017: ¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Keywordsメカノクロミズム / ねじれ / 立体配座 / 典型元素 / 熱活性化遅延蛍光 / 室温リン光 / 有機EL / ドナー・アクセプター / π共役 / 構造変化 / 光・電子物性
Outline of Annual Research Achievements

本研究では、前回参画した公募研究で得た知見を基に、構造的・電子的な「揺らぎ」がintrinsic、dynamic-π機能の鍵となる典型元素含有π電子共役分子を設計・創製することを目的とした。さらに、領域内・外の研究チームとの積極的な共同研究を通じて、外部刺激に 応答して電子受容性や発光色をダイナミックに変化できるelastic- π機能の実現を目指した。
今年度は、前年度に引き続き、代表者がこれまでに独自に開発してきた特異な構造を有する電子アクセプターを活用して、アルブレヒト健(A01班)および山本洋平(A02班)らと共同して開発したデンドリマー型ドナー・アクセプター・ドナー型分子の外部刺激に対する光物性挙動を調査した。その結果、湿度に応じて発色ならびに発光色が大きく変化することを見出した。また、IRやラマン分光測定から、これらがデンドリマー構造の変化に応じて引き起こされていることを示唆する結果を得た。また、以前開発した立体配座変化に応じて多色発光性メカノクロミズムを示す分子の固体状態における光物理過程をポーランドの国際共同研究で明らかにした。時間分解測定の結果、ドナーのアクセプターに対する配座に応じて熱活性化遅延蛍光、室温リン光、その両方、が入れ替わることを見出した。これを応用することで、ホスト材料に分散させた薄膜を調整する際に用いる溶媒の種類によって、配座の分布が変化し、発光挙動が著しく変化することを見出した。さらに、この知見を用いて、塗布プロセスをわずかに変えるだけで、有機ELデバイスの発光色を変調させることにも成功した。

Research Progress Status

平成30年度が最終年度であるため、記入しない。

Strategy for Future Research Activity

平成30年度が最終年度であるため、記入しない。

Report

(2 results)
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • Research Products

    (45 results)

All 2019 2018 2017 Other

All Int'l Joint Research (7 results) Journal Article (8 results) (of which Int'l Joint Research: 8 results,  Peer Reviewed: 8 results,  Open Access: 3 results) Presentation (29 results) (of which Int'l Joint Research: 11 results,  Invited: 13 results) Patent(Industrial Property Rights) (1 results)

  • [Int'l Joint Research] Durham University/Newcastle University(英国)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] Silesian University of Technology(ポーランド)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] Freiburg University/Dusseldorf University(ドイツ)

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

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] Durham University/Newcastle University(英国)

    • Related Report
      2017 Annual Research Report
  • [Int'l Joint Research] Silesian Technology University(ポーランド)

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

    • Related Report
      2017 Annual Research Report
  • [Journal Article] The impact of replacement of nitrogen with phosphorus atom in the pyromellitic diimides on their photophysical and electrochemical properties2019

    • Author(s)
      Pluczyk Sandra, Higginbotham Heather, Data Przemyslaw, Takeda Youhei, Minakata Satoshi
    • Journal Title

      Electrochemical Acta

      Volume: 295 Pages: 801-809

    • DOI

      10.1016/j.electacta.2018.10.156

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Ni(II) 10-Phosphacorrole: A Porphyrin Analogue Containing Phosphorus at the Meso Position2019

    • Author(s)
      Omori Hiroto、Hiroto Satoru、Takeda Youhei、Fliegl Heike、Minakata Satoshi、Shinokubo Hiroshi
    • Journal Title

      Journal of the American Chemical Society

      Volume: 141 Issue: 12 Pages: 4800-4805

    • DOI

      10.1021/jacs.8b13169

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Thermally activated delayed fluorescence vs. room temperature phosphorescence by conformation control of organic single molecules2019

    • Author(s)
      Data Przemyslaw, Okazaki Masato, Minakata Satoshi, Takeda Youhei
    • Journal Title

      Journal of Materials Chemistry C

      Volume: 印刷中 Issue: 22 Pages: 6616-6621

    • DOI

      10.1039/c9tc00909d

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Recent Advancements in and the Future of Organic Emitters:TADF- and RTP-Active Multifunctional Organic Materials2019

    • Author(s)
      Data Przemyslaw, Takeda Youhei
    • Journal Title

      Chemistry An Asian Journal

      Volume: 印刷中 Issue: 10 Pages: 1613-1636

    • DOI

      10.1002/asia.201801791

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Conformationally-flexible and moderately electron-donating units-installed D-A-D triad enabling multicolor-changing mechanochromic luminescence, TADF and room-temperature phosphorescence2018

    • Author(s)
      Takeda Youhei, Kaihara Takahito, Okazaki Masato, Higginbotham Heather, Data Przemyslaw, Tohnai, Norimitsu, Minakata Satoshi
    • Journal Title

      Chemical Communications

      Volume: 54 Issue: 50 Pages: 6847-6850

    • DOI

      10.1039/c8cc02365d

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Syntheses of Diverse Donor-Substituted Bisbenzofuro[2,3-b:3′,2′-e]pyridines (BBZFPys) via Pd Catalysis, and Their Photophysical Properties2018

    • Author(s)
      Itai Yuhei, Nishii Yuji, Stachelek Patrycja, Data Przemyslaw, Takeda Youhei, Minakata Satoshi, Miura Hasahiro
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 83 Issue: 17 Pages: 10289-10302

    • DOI

      10.1021/acs.joc.8b01451

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] FRET-mediated near infrared whispering gallery modes: studies on the relevance of intracavity energy transfer with Q-factor2018

    • Author(s)
      Osamu Oki, Soh Kushida, Annabel Mikosch, Kota Hatanaka, Youhei Takeda, Satoshi Minakata, Junpei Kuwabara, Takaki Kanbara, Thang Dao, Satoshi Ishii, Tadaaki Nagao, Alexander Kuhne, Felix Deschler, Richard Friend, Yohei Yamamoto
    • Journal Title

      Mater. Chem. Front.

      Volume: 2 Issue: 2 Pages: 270-274

    • DOI

      10.1039/c7qm00498b

    • NAID

      120007133837

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] An optical and electrical study of full thermally activated delayed fluorescent white organic light-emitting diodes2017

    • Author(s)
      Pereira Daniel de Sa、dos Santos Paloma L.、Ward Jonathan S.、Data Przemyslaw、Okazaki Masato、Takeda Youhei、Minakata Satoshi、Bryce Martin R.、Monkman Andrew P.
    • Journal Title

      Scientific Reports

      Volume: 7 Issue: 1

    • DOI

      10.1038/s41598-017-06568-3

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Presentation] Dibenzo[a,j]phenazine-Cored Donor-Acceptor-Donor Triads as Multifunctional Luminescent Materials2019

    • Author(s)
      Youhei Takeda
    • Organizer
      the Pure and Applied Chemistry International Conference 2019 (PACCON 2019)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Development of Multi-photofunctional Organic Molecular Materials Driven by the Discovery of New Reaction and Molecular Scaffold2019

    • Author(s)
      Youhei Takeda
    • Organizer
      第14回柴崎研コロキウム
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Dibenzo[a,j]phenazine-Cored Twisted Donor-Acceptor-Donor Triads: A Promising Platform for TADF, RTP, and Mechanochromic Luminescence2019

    • Author(s)
      Youhei Takeda
    • Organizer
      7th International Symposium on π-System Figuration および 領域成果報告会
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 新奇ドナー・アクセプター系 π 共役分子を活用した次世代発光分子材料の創製2018

    • Author(s)
      武田洋平
    • Organizer
      筑波大学 数理物質系物質科学セミナー
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 熱活性化遅延蛍光を示すD-A-D-A型π共役マクロサイクルの構造と物性2018

    • Author(s)
      和泉彩香, Heather Higginbotham, Sandra Pluczyk, Przemyslaw Data, 武田洋平, 南方聖司
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] ジベンゾフェナジンを電子アクセプターとするD-A-D型の新規発光分子の創成2018

    • Author(s)
      武田洋平, 岡崎真人, Data Przemyslaw, Monkman Andrew, 南方聖司
    • Organizer
      第5回π造形科学若手研究会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 分子の「動き」をいかす材料開発2018

    • Author(s)
      武田洋平
    • Organizer
      第8回CSJ化学フェスタ
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Conformation-Dictated Regulation of Luminescent Properties of TADF-Active Twisted Donor-Acceptor-Donor Triads in Solid States2018

    • Author(s)
      Youhei Takeda
    • Organizer
      π-System Figuration European-Japanese Workshop 2018 (π-EJ 2018)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Conformation-Dictated Regulation of Luminescence Properties of Dibenzo[a,j]phenazine-Cored Twisted Donor-Acceptor-Donor Triads2018

    • Author(s)
      Youhei Takeda
    • Organizer
      10th Singapore International Chemistry Conference (SICC10)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 新奇反応が拓く次世代発光分子材料の創成と応用2018

    • Author(s)
      武田洋平
    • Organizer
      岡山大学若手研究者育成事業 第1回講演会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Dibenzo[a,j]phenazines (DBPHZs): Useful Scaffold for Multifunctional Luminescent Materials in Optoelectonics2018

    • Author(s)
      Youhei Takeda
    • Organizer
      The 5th Workshop on Organic Electronics and Nanophotonics (WOREN 2018)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 電子ドナーにリン原子架橋ユニットを有するD-A-D型ジベンゾフェナジンの構造ならびに外部刺激に対する発光特性変化2018

    • Author(s)
      開原崇仁,Higginbotham Heather, Data Przemyslaw, 武田洋平,南方聖司
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ジベンゾフェナジンを電子アクセプターとするD-A-D-A型π共役マクロサイクルの物性と有機EL発光材料としての応用2018

    • Author(s)
      和泉彩香,Higginbotham Heather, Data Przemyslaw, 武田洋平,南方聖司
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ジアザ[5]ヘリセンを電子アクセプターとするねじれ型D-A-Dπ共役分子の合成と物理化学的特性2018

    • Author(s)
      井狩優太,Bovenkerk Marcel, 武田洋平, Esser Birgit, 南方聖司
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Dibenzo[a,j]phenazine-cored Perpendicularly Twisted Donor-Acceptor-Donor Systems as Value-added Thermally Activated Delayed Fluorescence (TADF) Materials2017

    • Author(s)
      Youhei Takeda
    • Organizer
      The 10th China-Japan Joint Symposium on Functional Supramolecular Systems
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthetic Toolboxes for Constructing Donor-Acceptor-based Efficient TADF Materials2017

    • Author(s)
      Youhei Takeda
    • Organizer
      XXIInd International Krutyn Summer School (IKSS2017) ~State of the Art in Organic-only TADF OLEDs. From Theory to Applications~
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Dibenzo[a,j]phenazine: A Useful Building Block for Efficient and Value-added Thermally Activated Delayed Fluorescence (TADF) Materials2017

    • Author(s)
      Youhei Takeda, Masato Okazaki, Przemyslaw Data, Andrew P. Monkman, Satoshi Minakata
    • Organizer
      17th International Symposium on Novel Aromatic Compounds (ISNA 2017)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Physicochemical Properites of Phosphorus-Containing D-A-D Type Dibenzo[a,j]phenazines2017

    • Author(s)
      Takahito Kaihara, Youhei Takeda, Satoshi Minakata
    • Organizer
      17th International Symposium on Novel Aromatic Compounds (ISNA 2017)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Physicochemical Properties of D-A-D-A Type π-Conjugated Macrocycles employing Dibenzo[a,j]phenazines as Acceptors2017

    • Author(s)
      Saika Izumi, Youhei Takeda, Satoshi Minakata
    • Organizer
      17th International Symposium on Novel Aromatic Compounds (ISNA 2017)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ビナフタレンジアミン類の酸化的変換反応開発を基軸とする「個性」溢れる発光性π共役分子の創成2017

    • Author(s)
      武田洋平
    • Organizer
      第49回構造有機化学若手の会 夏の学校
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] リン原子をドナーユニットに有するD-A-D型ジベンゾ[a,j]フェナジン誘導体の合成と物理化学的性質2017

    • Author(s)
      開原崇仁, 武田洋平, 南方聖司
    • Organizer
      第49回構造有機化学若手の会 夏の学校
    • Related Report
      2017 Annual Research Report
  • [Presentation] 分子の捻れ・柔軟性を活用した発光性分子の創成2017

    • Author(s)
      武田洋平
    • Organizer
      第6回 化学フロンティア研究会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] ジベンゾ[a,j]フェナジンをアクセプターに有するD-A-D-A型π共役マクロサイクルの合成・構造、及び物理化学的性質2017

    • Author(s)
      和泉彩香, 武田洋平, 南方聖司
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] メゾ位にヘテロ原子を含む新規ポルフィリノイドの合成2017

    • Author(s)
      大森裕土, 廣戸 聡, 武田洋平, 南方聖司, 忍久保洋
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 圧力および温度に敏感な色変化を示すπ共役デンドリマー集合体2017

    • Author(s)
      中嶋紗英, アルブレヒト建, 武田洋平, 南方聖司, 山元公寿, 山本洋平
    • Organizer
      第66回高分子討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 芳香族アミン類の酸化的変換反応による熱活性化遅延蛍光分子の創成2017

    • Author(s)
      武田洋平
    • Organizer
      ITbM/IGER Chemistry Workshop 2017
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 新奇な酸化的分子変換反応が拓く次世代発光材料の創成2017

    • Author(s)
      武田洋平
    • Organizer
      島津製作所 講演会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Dibenzo[a,j]phenazine-Cored Twisted Donor-Acceptor-Donor Triads as Value-Added Thermally Activated Delayed Fluorescence (TADF) Materials2017

    • Author(s)
      Youhei Takeda
    • Organizer
      4th International Symposium on π-System Figuration (German-Japanese Workshop Heidelberg)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ジベンゾ[a,j]フェナジンをアクセプターに有するD-A-D型π共役マクロサイクルの合成・構造および物理化学的特性2017

    • Author(s)
      和泉彩香, 武田洋平, 南方聖司
    • Organizer
      第4回π造形科学若手研究会
    • Related Report
      2017 Annual Research Report
  • [Patent(Industrial Property Rights)] 有機EL材料および有機ELデバイス2018

    • Inventor(s)
      武田洋平、南方聖司、コール ヘザー、ダータ プシュミシュワフ
    • Industrial Property Rights Holder
      国立大学法人大阪大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2018-164702
    • Filing Date
      2018
    • Related Report
      2018 Annual Research Report

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Published: 2017-04-28   Modified: 2019-12-27  

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