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Development of high-performance semiconductor molecules utilizing molecular and electronic skeletons of phenacenes

Research Project

Project/Area Number 20K05648
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 35030:Organic functional materials-related
Research InstitutionOkayama University

Principal Investigator

Okamoto Hideki  岡山大学, 自然科学学域, 准教授 (30204043)

Co-Investigator(Kenkyū-buntansha) 山路 稔  群馬大学, 大学院理工学府, 准教授 (20220361)
Project Period (FY) 2020-04-01 – 2023-03-31
Project Status Completed (Fiscal Year 2022)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2022: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2021: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2020: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords有機半導体 / フェナセン / 電界効果型トランジスタ / FET / 多環芳香族化合物 / 電子スペクトル / 光化学反応 / 有機物半導体 / ヘリセン / ロジック回路
Outline of Research at the Start

高性能有機半導体材料はユビキタス電子デバイス構築に不可欠な基盤である.この背景から本申請課題では,フェナセン及び類縁π拡張芳香族炭化水素のπ電子骨格を活用し,有機半導体候補化合物を設計・合成する.光環化反応を鍵反応として新フェナセン分子を効率的に構築する.電界効果型トランジスタ(FET)デバイスを作成し,動作特性評価と分子設計へのフィードバックを通して新しい高性能有機FET材料の創出を目指す.

Outline of Final Research Achievements

Development of new high-performance organic semiconductors is one of the central issues in organic electronics. In this study, synthesis of novel phenacene-based organic semiconductors and their performance of active layers in field-effect transistor devices were investigated. The phenacene molecules were successfully synthesized through Mallory photoreactions of the corresponding diarylethene precursors. On the bases of the relationships between the phenacene structures and the performance of organic semiconductors, factors for designing a future high-performance organic semiconductors were obtained.

Academic Significance and Societal Importance of the Research Achievements

有機半導体材料は,柔軟,軽量で材料設計の自由度が高ことなどの多くの利点を有しているが,安定で高性能な材料はいまだに限られているのが現状である.本研究で得られた有機半導体材料の高移動度化に対する指針は,耐久性があり,高性能な未来の有機半導体を開発するために有効であると考えられる.特にフェナセンは,従来の有機分子に比べて安定であるため,耐久性のある有機電子デバイスの作製に展開できる可能性があると期待される.

Report

(4 results)
  • 2022 Annual Research Report   Final Research Report ( PDF )
  • 2021 Research-status Report
  • 2020 Research-status Report
  • Research Products

    (31 results)

All 2023 2022 2021 2020

All Journal Article (11 results) (of which Int'l Joint Research: 5 results,  Peer Reviewed: 10 results,  Open Access: 4 results) Presentation (19 results) (of which Int'l Joint Research: 2 results,  Invited: 2 results) Book (1 results)

  • [Journal Article] Star-burst polycyclic aromatic hydrocarbons prepared by multi-photocyclization and the photophysical features2023

    • Author(s)
      Yamaji Minoru、Okamoto Hideki
    • Journal Title

      Journal of Photochemistry and Photobiology A: Chemistry

      Volume: 436 Pages: 114387-114387

    • DOI

      10.1016/j.jphotochem.2022.114387

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Solvent-dependent fluorescence behaviour of imide-fused [<i>n</i>]phenacenes (<i>n</i> = 3, 5, 7)2023

    • Author(s)
      Nose Keito、Yoshioka Kaito、Yamaji Minoru、Tani Fumito、Goto Kenta、Okamoto Hideki
    • Journal Title

      RSC Advances

      Volume: 13 Issue: 6 Pages: 4096-4101

    • DOI

      10.1039/d2ra07771j

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Fabrication and characterization of thin-film field-effect transistors with alkyl-phenyl[n]phenacenes (n=4-6)2022

    • Author(s)
      Zhang, Yanting; Eguchi, Ritsuko; Okamoto, Hideki; Goto, Kenta; Tani, Fumito; Yamaji, Minoru; Goto, Hidenori; Kubozono, Yoshihiro
    • Journal Title

      J. Mater. Chem. C

      Volume: 10 Issue: 43 Pages: 16309-16320

    • DOI

      10.1039/d2tc03383f

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis of 2,3-Anthracenedicarboxylic-acid-derived Fluorophore and Chemiluminophore Incorporating Dipicolylaminomethyl Receptors, and Their Luminescence Responses to Metal Ions2022

    • Author(s)
      Okamoto Hideki、Yamazaki Naomi、Matsui Ayako、Satake Kyosuke
    • Journal Title

      HETEROCYCLES

      Volume: 104 Issue: 9 Pages: 1614-1614

    • DOI

      10.3987/com-22-14703

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Charge transport capabilities of dibenzo[n]phenacenes (n = 5窶?7): influence of trap states and molecular packing2022

    • Author(s)
      Y. Zhang, S. Hamao, H. Goto, Y. Kubozono, H. Okamoto, K. Sugimoto, N. Yasuda, A. Fujiwara, R. Eguchi
    • Journal Title

      J. Phys. Chem. C

      Volume: 126 Issue: 44 Pages: 18849-18854

    • DOI

      10.1021/acs.jpcc.2c04879

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Evaluation of Effective Field-Effect Mobility in Thin-Film and Single-Crystal Transistors for Revisiting Various Phenacene-Type Molecules2022

    • Author(s)
      Y. Zhang, R. Eguchi, S. Hamao, H. Okamoto, H. Goto, Y. Kubozono
    • Journal Title

      ACS omega

      Volume: 7 Issue: 6 Pages: 5495-5501

    • DOI

      10.1021/acsomega.1c06932

    • Related Report
      2021 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Solid-state photoluminescence of biaryls: Relationship between photophysical feature and crystal structure2021

    • Author(s)
      Yamaji Minoru、Okamoto Hideki、Goto Kenta、Tani Fumito
    • Journal Title

      Journal of Photochemistry and Photobiology A: Chemistry

      Volume: 421 Pages: 113518-113518

    • DOI

      10.1016/j.jphotochem.2021.113518

    • Related Report
      2021 Research-status Report
    • Peer Reviewed
  • [Journal Article] N-Hをプロトンドナーとする励起状態分子内プロトン移動(ESIPT)蛍光色素の最近の展開2021

    • Author(s)
      岡本秀毅
    • Journal Title

      光化学

      Volume: 53 Pages: 124-130

    • NAID

      40022780783

    • Related Report
      2021 Research-status Report
  • [Journal Article] Fabrication of ring oscillators using organic molecules of phenacene and perylenedicarboximide2021

    • Author(s)
      Fioravanti Niko、Pierantoni Luca、Mencarelli Davide、Turchetti Claudio、Hamao Shino、Okamoto Hideki、Goto Hidenori、Eguchi Ritsuko、Fujiwara Akihiko、Kubozono Yoshihiro
    • Journal Title

      RSC Advances

      Volume: 11 Issue: 13 Pages: 7538-7551

    • DOI

      10.1039/d1ra00511a

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Photochemical synthesis and device application of acene-phenacene hybrid molecules, dibenzo[n]phenacenes (n = 5-7)2021

    • Author(s)
      Yanting Zhang, Ritsuko Eguchi, Shino Hamao, Kenta Goto, Fumito Tani, Minoru Yamaji, Yoshihiro Kubozono, and Hideki Okamoto
    • Journal Title

      Chemical Communications

      Volume: 57

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Facile synthesis of picenes incorporating imide moieties at both edges of the molecule and their application to n-channel field-effect transistors2020

    • Author(s)
      Guo Yuxin、Yoshioka Kaito、Hamao Shino、Kubozono Yoshihiro、Tani Fumito、Goto Kenta、Okamoto Hideki
    • Journal Title

      RSC Advances

      Volume: 10 Issue: 52 Pages: 31547-31552

    • DOI

      10.1039/d0ra06629j

    • NAID

      120006891216

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Presentation] ベンゼンスルホンアミドをプロトンドナーとするフタルイミドのESIPT 蛍光挙動2023

    • Author(s)
      多月あおい,山路 稔,岡本秀毅
    • Organizer
      日本化学会第103春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] イミド置換基で修飾したフェナセン誘導体の合成および蛍光特性2023

    • Author(s)
      野勢勁斗,吉岡海渡,山路 稔,五島健太,谷 文都,岡本秀毅
    • Organizer
      日本化学会第103春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 分子長軸両端にイミド官能基を持つ[n]フェナセン誘導体(n=3, 5, 7)の合成および蛍光特性2022

    • Author(s)
      野勢勁斗,吉岡海渡,山路 稔,五島健太,谷 文都,岡本秀毅
    • Organizer
      2022年光化学討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 環状及び非環状スルホンアミド構造を持つフタルイミド類の ESIPT 蛍光特性2022

    • Author(s)
      多月あおい,伊谷一将,西村賢宣,山路 稔,岡本秀毅
    • Organizer
      2022年光化学討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] Relationship between fluorescence in the solid state and the crystal structures of diphenylnaphthalenes2022

    • Author(s)
      Minoru Yamaji, Hideki Okamoto, Kengo Ssuzuki, Kengo, Toshiki Mutai, Isao Yoshikawa, Hirohiko Houjou
    • Organizer
      2022年光化学討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] Photochemical Synthesis of Phenacenes and Their Application to Organic Electronics2022

    • Author(s)
      Hideki Okamoto
    • Organizer
      International Conference on Organic and Applied Chemistry 2022
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] スルホンアミドをプロトンドナーとする ESIPT 蛍光色素の発光挙動2022

    • Author(s)
      多月あおい,伊谷一将,西村賢宣,山路 稔,岡本秀毅
    • Organizer
      2022年日本化学会中国四国支部大会広島大会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 環状及び非環状のスルホンアミドをプロトンドナーとするフタルイミド類のESIPT 蛍光特性2022

    • Author(s)
      多月あおい,伊谷一将,西村賢宣,山路 稔,岡本秀毅
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] イミド官能基を持つフェナセン誘導体の合成および蛍光特性2022

    • Author(s)
      野勢勁斗,吉岡海渡,山路 稔,五島健太,谷 文都,岡本秀毅
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Research-status Report
  • [Presentation] 分子長軸の両端にイミド基を持つフェナセン誘導体の蛍光の溶媒応答2021

    • Author(s)
      吉岡海渡,山路 稔,五島健太,谷 文都,岡本秀毅
    • Organizer
      2021年光化学討論会
    • Related Report
      2021 Research-status Report
  • [Presentation] スルホンアミドをプロトンドナーとするフタルイミド類のESIPT蛍光特性2021

    • Author(s)
      多月あおい,伊谷一将,山路 稔,岡本秀毅
    • Organizer
      2021年光化学討論会
    • Related Report
      2021 Research-status Report
  • [Presentation] ビアリル分子の固体発光と結晶構造の関連性について2021

    • Author(s)
      山路 稔,岡本秀毅,五島健太,谷 文都
    • Organizer
      2021年光化学討論会
    • Related Report
      2021 Research-status Report
  • [Presentation] Fluorescence manipulation of amino- and amido-substituted phthalimides and naphthalimides based on ICT and ESIPT features2021

    • Author(s)
      Hideki Okamoto
    • Organizer
      Symposium on Organic and Applied Chemistry 2021
    • Related Report
      2021 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Organic field-effect transistors based on newly synthesized dibenzo[n]phenacenes (n = 5 - 7)2021

    • Author(s)
      Y. Zhang, R. Eguchi, S. Hamao, K. Goto, F. Tani, M. Yamaji, Y. Kubozono, and H. Okamoto
    • Organizer
      2021年第68回応用物理学会春季学術講演会
    • Related Report
      2020 Research-status Report
  • [Presentation] 分子長軸の両端にイミド部位を持つπ拡張フェナセン誘導体の合成研究2020

    • Author(s)
      吉岡海渡,岡本秀毅
    • Organizer
      2020日本化学会中国四国支部大会島根大会
    • Related Report
      2020 Research-status Report
  • [Presentation] Photochemical Synthesis of Picenes Incorporating Imide Moieties at the both Edges of the Molecule and their Application to n-Channel Field-Effect Transistors2020

    • Author(s)
      Yuxin Guo, Kaito Yoshioka, Shino Hamao, Yoshihiro Kubozono, Fumito Tani, Kenta Goto, Hideki Okamoto
    • Organizer
      第10回CSJ化学フェスタ2020
    • Related Report
      2020 Research-status Report
  • [Presentation] 長鎖アルキル基を有するπ拡張フェナセンの合成: 高性能FET材料の開拓2020

    • Author(s)
      小笹景子,浜尾志乃,久保園芳博,谷 文都,五島健太,岡本秀毅
    • Organizer
      第10回CSJ化学フェスタ2020
    • Related Report
      2020 Research-status Report
  • [Presentation] 両端にドナーおよびアクセプター置換基を有する[7]ヘリセン誘導体の合成および電子スペクトル2020

    • Author(s)
      中塚智子,岡本秀毅
    • Organizer
      2020年Web光化学討論会
    • Related Report
      2020 Research-status Report
  • [Presentation] マルチクロモファー化による芳香族分子の発光特性への影響2020

    • Author(s)
      山路 稔,岡本秀毅,加藤真一郎
    • Organizer
      2020年Web光化学討論会
    • Related Report
      2020 Research-status Report
  • [Book] 有機光反応の化学(執筆担当部分:12章シクロファン類の光反応)2022

    • Author(s)
      日本化学会
    • Total Pages
      216
    • Publisher
      化学同人
    • ISBN
      9784759814033
    • Related Report
      2021 Research-status Report

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Published: 2020-04-28   Modified: 2024-01-30  

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