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Challenge for constructing novel organic electronic materials utilizing phenacene as the extended pi-motif

Research Project

Project/Area Number 17K05976
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic and hybrid materials
Research InstitutionOkayama University

Principal Investigator

Okamoto Hideki  岡山大学, 自然科学研究科, 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) 2017-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2019: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2018: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2017: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords有機エレクトロニクス / フェナセン / 電界効果型トランジスタ / 光化学反応 / 多環芳香族化合物 / FET / 有機電子材料 / 光環化反応 / 有機半導体 / OFET / 発光材料 / 多環状芳香族化合物 / 有機半導体材料 / 有機発光材料 / 芳香族化合物 / 電子材料
Outline of Final Research Achievements

High performance organic semiconductors have been desired in current organic electronics. In the present study, synthetic strategy of functionalized phenacenes as novel organic semiconductors was established. Namely, Mallory photoraction was used as the key step of constructing phenacene frameworks. Field-effect transistors were fabricated by using the synthesized phenacenes and their performance was evaluated to demonstrate that the phenacene-based organic semiconductors were promising as active layer of FETs. The results obtained in this project will significantly contribute for molecular design and fubrication of future high-performance FET materials.

Academic Significance and Societal Importance of the Research Achievements

高度にπ拡張されたフェナセンや,適切に機能化されたフェナセンの合成は一般に困難であるが,合成の最終段階にMallory光反応を活用して種々の機能化フェナセンを合成する手法を確立した.合成したフェナセンは,高性能FETデバイスの活性層として有効であることを実験的に示すことができた.また,フェナセンをp型半導体として用い,有機演算回路を構築することも可能になった.現在,高性能有機半導体材料は,軽量・超小型電子デバイスの作製などのために社会的にも渇望されている.本研究課題の成果は,有機半導体分子の設計や供給の観点から学術的,社会的に寄与すると期待される.

Report

(5 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • 2017 Research-status Report
  • Research Products

    (44 results)

All 2021 2020 2019 2018 2017 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: 3 results) Presentation (23 results) (of which Int'l Joint Research: 7 results,  Invited: 4 results) Book (3 results)

  • [Int'l Joint Research] Universita Politecnica della Marche(イタリア)

    • Related Report
      2020 Annual Research Report
  • [Int'l Joint Research] University of Strathclyde(英国)

    • Related Report
      2019 Research-status Report
  • [Int'l Joint Research] National Tsing Hua University(その他の国・地域)

    • Related Report
      2019 Research-status Report
  • [Int'l Joint Research] National Tsing Hua University(台湾)

    • Related Report
      2018 Research-status Report
  • [Int'l Joint Research] Universita Politecnica della Marche(イタリア)

    • Related Report
      2018 Research-status Report
  • [Int'l Joint Research] National Tsing Hua University(Taiwan)

    • Related Report
      2017 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 Annual Research 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

      Chem. Commun.

      Volume: 57 Issue: 39 Pages: 4768-4771

    • DOI

      10.1039/d1cc01294k

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [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 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Synthesis of [7]phenacene incorporating tetradecyl chains in the axis positions and its application in field-effect transistors2020

    • Author(s)
      Hideki Okamoto, Shino Hamao, Keiko Kozasa, Yanan Wang, Yoshihiro Kubozono, Yong-He Pan, Yu-Hsiang Yen, Germar Hoffmann, Fumito Tani, Kenta Goto
    • Journal Title

      Journal of Materials Chemistry C

      Volume: 8 Issue: 22 Pages: 7422-7435

    • DOI

      10.1039/d0tc00272k

    • NAID

      120007027581

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Blue fluorescence from N,O-coordinated BF2 complexes having aromatic chromophores in solution and solid state2019

    • Author(s)
      Minoru Yamaji, Kazuhiro Tomonari, Keisuke Ikuma, Kenta Goto, Fumito Tani, Hideki Okamoto
    • Journal Title

      Photochem. Photobiol. Sci.

      Volume: 18 Issue: 12 Pages: 2884-2892

    • DOI

      10.1039/c9pp00410f

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Fluorescence properties of amido-substituted 2,3-naphthalimides: Excited-state intramolecular proton transfer (ESIPT) fluorescence and responses to Ca2+ ions2019

    • Author(s)
      Lei Wang, Mayu Fujii, Misa Namba, Minoru Yamaji, Hideki Okamoto
    • Journal Title

      Tetrahedron Lett.

      Volume: 60 Issue: 43 Pages: 151189-151189

    • DOI

      10.1016/j.tetlet.2019.151189

    • NAID

      120007163673

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Low-voltage organic thin-film transistors based on [n]phenacenes2019

    • Author(s)
      Afra Al Ruzaiqi, Hideki Okamoto, Yoshihiro Kubozono, Ute Zschieschang, Hagen Klauk, Peter Baran, Helena Gleskova
    • Journal Title

      Org. Electron.

      Volume: 73 Pages: 286-291

    • DOI

      10.1016/j.orgel.2019.06.021

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Fabrication of flexible high-performance organic field-effect transistors using phenacene molecules and their application toward flexible CMOS inverters2019

    • Author(s)
      Pompei Emanuela、Turchetti Claudio、Hamao Shino、Miura Akari、Goto Hidenori、Okamoto Hideki、Fujiwara Akihiko、Eguchi Ritsuko、Kubozono Yoshihiro
    • Journal Title

      Journal of Materials Chemistry C

      Volume: 印刷中 Issue: 20 Pages: 6022-6033

    • DOI

      10.1039/c8tc05824e

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis of the extended phenacene molecules, [10]phenacene and [11]phenacene, and their performance in a field-effect transistor2019

    • Author(s)
      Okamoto Hideki、Hamao Shino、Eguchi Ritsuko、Goto Hidenori、Takabayashi Yasuhiro、Yen Paul Yu-Hsiang、Liang Luo Uei、Chou Chia-Wei、Hoffmann Germar、Gohda Shin、Sugino Hisako、Liao Yen-Fa、Ishii Hirofumi、Kubozono Yoshihiro
    • Journal Title

      Scientific Reports

      Volume: 9 Issue: 1 Pages: 4009-4009

    • DOI

      10.1038/s41598-019-39899-4

    • NAID

      120006777515

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Fluorescence behaviour of 2-, 3- and 4-amino-1,8-naphthalimides: effects of the substitution positions of the amino functionality on the photophysical properties2018

    • Author(s)
      Wang Lei、Fujii Mayu、Yamaji Minoru、Okamoto Hideki
    • Journal Title

      Photochemical & Photobiological Sciences

      Volume: 17 Issue: 10 Pages: 1319-1328

    • DOI

      10.1039/c8pp00302e

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of isomeric coumarin-fluorene hybrids by photocyclization and the photophysical features2018

    • Author(s)
      Yamaji Minoru、Okamoto Hideki、Goto Kenta、Kato Shin-ichiro、Tani Fumito、Nakamura Yosuke
    • Journal Title

      Tetrahedron Letters

      Volume: 59 Issue: 13 Pages: 1216-1219

    • DOI

      10.1016/j.tetlet.2018.02.033

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Photophysical features of naphthols having esters, formyl and acetyl groups and the difluoroboronated complex in solution and the solid state2018

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

      Journal of Photochemistry and Photobiology A: Chemistry

      Volume: 印刷中 Pages: 1010-6030

    • DOI

      10.1016/j.jphotochem.2018.04.017

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [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 Annual Research 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 Annual Research 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 Annual Research 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 Annual Research 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 Annual Research 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 Annual Research Report
  • [Presentation] ピセンジイミド誘導体の合成とn-型半導体特性2020

    • Author(s)
      吉岡海渡,郭玉金,浜尾志乃,久保園芳博,岡本秀毅
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] Synthesis, Electronic Spectra, and Transistor Application of π-Extended Phenacenes2019

    • Author(s)
      Hideki Okamoto
    • Organizer
      International Conference on Photocatalysis and Photoenergy 2019 (ICoPP2019)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Photochemical synthesis of phenacenes and the application to OFET devices2019

    • Author(s)
      Hideki Okamoto
    • Organizer
      The 3rd OU-SKKU Bilateral Symposium on Photofunctional Materials and Nanointerfaces
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Blue fluorescence from N,O-coodinated BF2 complexes having aromatic chromophores in solution and solid state2019

    • Author(s)
      Minoru Yamaji, Hideki Okamoto, Kenta Goto, Fumito Tani
    • Organizer
      The 12th Taiwan-Japan Bilateral Symposium on Architecture of Functional Organic Molecules
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] 高性能有機半導体材料の開拓を指向する3,12-ジテトラデシル[7]フェナセンの合成2019

    • Author(s)
      小笹景子,浜尾志乃,久保園芳博,郷田慎,岡本秀毅
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] 末端にイミドを導入したピセン誘導体の合成研究2019

    • Author(s)
      吉岡海渡,郭玉金,浜尾志乃,久保園芳博,岡本秀毅
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] 高性能FET材料開拓を目指した長鎖アルキル基を有するπ拡張フェナセンの合成2019

    • Author(s)
      小笹景子,浜尾志乃,久保園芳博,岡本秀毅
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] Photochemical Synthesis of Diimide Derivatives of Picene as Potential n-type OFET Material2019

    • Author(s)
      Yuxin Guo, Kaito Yoshioka, Yoshihiro Kubozono, Shino Hamao, and Hideki Okamoto
    • Organizer
      9th Annual Basic Science International Conference 2019 (BaSIC 2019)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Photophysical features of naphthols having esters, formyl and acetyl groups and the difluoroboronated complex in solution and the solid state2018

    • Author(s)
      Minoru Yamaji, Hideki Okamoto, Kenta Goto, Fumito, Tani
    • Organizer
      2018年光化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] π共役拡張フェナセンの光環化による合成と電子スペクトル特性2018

    • Author(s)
      岡本秀毅,久保園芳博,浜尾志乃,郷田 慎,杉野久子,山路 稔
    • Organizer
      2018年光化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] Photochemical synthesis and electronic spectra of extremely π-extended phenacenes2018

    • Author(s)
      Hideki Okamoto
    • Organizer
      The 11th Japan-Taiwan Bilateral Symposium on Architecture of Functional Organic Molecules
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Photophysical features of naphthols having esters, formyl and acetyl groups and the difluoroboronated complex in solution and the solid state2018

    • Author(s)
      Minoru Yamaji, Hideki Okamoto, Kenta Goto and Fumito Tani
    • Organizer
      The 11th Japan-Taiwan Bilateral Symposium on Architecture of Functional Organic Molecules
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] 光環化反応を用いる長大なπ共役拡張フェナセンの合成とスペクトル特性2018

    • Author(s)
      岡本秀毅
    • Organizer
      2018年有機光化学研究会
    • Related Report
      2018 Research-status Report
  • [Presentation] ジフェニルフェナンスリルエテンから光環化反応により生成するベンゼン環7つからなる縮環化合物の研究2017

    • Author(s)
      山路 稔,岡本秀毅,務台俊樹,吉川 勲,北條博彦,谷 文都
    • Organizer
      2017年光化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] Wittig反応-Mallory光環化シーケンシャルフロー合成によるフェナセン骨格の簡便かつ系統的な構築2017

    • Author(s)
      高橋晴彦,岡本秀毅
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] Synthesis of π-extended phenacenes by photocyclization of diarylethenes and their transistor application2017

    • Author(s)
      Hideki Okamoto, Yoshihiro Kubozono, and Minoru Yamaji
    • Organizer
      2017 Global Research Efforts on Energy and Nanomaterials
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 連続光フロー反応によるフェナセンの簡便合成と機能化フェナセンへの展開2017

    • Author(s)
      高橋晴彦,岡本秀毅
    • Organizer
      2017年日本化学会中国四国支部大会鳥取大会
    • Related Report
      2017 Research-status Report
  • [Book] Physics and Chemistry of Carbon-Based Materials (Yoshihiro Kubozono Ed.) (Chap. 7 Organic Chemistry of π-Conjugated Polycyclic Aromatic Hydrocarbons: Acenes and Phenacenes)2019

    • Author(s)
      Hideki Okamoto
    • Total Pages
      332
    • Publisher
      Springer
    • ISBN
      9789811334160
    • Related Report
      2018 Research-status Report
  • [Book] Light-Active Functional Organic Materials (Hiroko Yamada and Shiki Yagai Eds.) (Chap. 10 Photochemical Synthesis of Phenacenes and Their Application to Organic Semiconductors)2019

    • Author(s)
      Hideki Okamoto and Yoshihiro Kubozono
    • Total Pages
      218
    • Publisher
      Pan Stanford Publishing Pte. Ltd.
    • ISBN
      9789814800150
    • Related Report
      2018 Research-status Report
  • [Book] 5)「プリンテッド・エレクトロニクスに向けた材料、作製プロセス技術の開発と最新事例」[第3章,高移動度な有機半導体材料の開発,第3節「光フロー反応を用いた高次フェナセンの効率的合成と有機半導体トランジスタへの応用」]2017

    • Author(s)
      岡本秀毅,久保園芳博
    • Total Pages
      528
    • Publisher
      技術情報協会
    • ISBN
      9784861046810
    • Related Report
      2017 Research-status Report

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Published: 2017-04-28   Modified: 2022-08-18  

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