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Photochemical conversion of small aromatic chromophores into polycyclic frameworks

Research Project

Project/Area Number 24550054
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionOkayama University

Principal Investigator

OKAMOTO Hideki  岡山大学, 自然科学研究科, 准教授 (30204043)

Co-Investigator(Renkei-kenkyūsha) YAMAJI Minoru  群馬大学, 大学院理工学研究府, 准教授 (20220361)
Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥5,590,000 (Direct Cost: ¥4,300,000、Indirect Cost: ¥1,290,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2013: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2012: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
Keywords光反応 / 光環化 / 光付加 / 多環状化合物 / 芳香族化合物 / シクロファン / ベンゼンダイマー / フェナセン / フロー反応 / 有機物半導体 / 合成化学 / 光物性 / アザシクロファン / 置換基効果
Outline of Final Research Achievements

Photochemical conversion of small aromatic chromophores, e.g. benzene, naphthalene, phenanthrene, etc., into polycyclic frameworks have been investigated.
(1) For the photoreaction of azacyclophanes incorporating two benzene chromophores, benzene photodimerization took place to afford various polycyclic skeletons. Depending on the substituents on the benzene rings, we have observed formation of p,p'-dibenzene, octahedrane, and cage diene benzene dimers. Relative energies of the benzene dimer were evaluated by theoretical calculation to have insight into the substituent effects.
(2) Diarylethenes, incorporating benzene, naphthalene, or phenanthrene chromophores, were converted into polycyclic aromatic frameworks, namely phenacenes in which the benzene rings were fused in a zigzag array. By applying a continuous flow photoreaction technique, various phenacenes were successfully synthesized with high chemical yield.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (30 results)

All 2015 2014 2013 2012 Other

All Journal Article (7 results) (of which Peer Reviewed: 6 results,  Open Access: 3 results,  Acknowledgement Compliant: 3 results) Presentation (23 results) (of which Invited: 3 results)

  • [Journal Article] Photophysical and photochemical processes of excited singlet and triplet [3n]cyclophanes (n = 2–6) studied by emission measurements, steady-state and laser flash photolyses2015

    • Author(s)
      Minoru Yamaji, Hideki Okamoto, Yuhko Hakoshima and Teruo Shinmyozu
    • Journal Title

      Journal of Physical Chemistry, A

      Volume: 119 Issue: 10 Pages: 1867-1874

    • DOI

      10.1021/jp511105v

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] An expanded phenacene-type molecule, [8]phenacene: synthesis and transistor application2014

    • Author(s)
      Hideki Okamoto, Ritsuko Eguchi, Shino Hamao, Hidenori Goto, Kazuma Gotoh, Masanari Izumi, Yutaka Takaguchi, Shin Gohda, Yoshihiro Kubozono
    • Journal Title

      Scientific Reports

      Volume: 4 Issue: 1 Pages: 5330-5330

    • DOI

      10.1038/srep05330

    • Related Report
      2014 Annual Research Report 2013 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Photochemical synthesis of diphenylphenanthrenes, and the photophysical properties studied by emission and transient absorption measurements2014

    • Author(s)
      Minoru Yamaji, Yuuma Hakoda, Ami Horimoto and Hideki Okamoto
    • Journal Title

      Rapid Communication in Photoscience

      Volume: 3 Issue: 4 Pages: 73-75

    • DOI

      10.5857/rcp.2014.3.4.73

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Efficient Synthetic Photocyclization for Phenacenes Using a Continuous Flow Reactor2014

    • Author(s)
      H. Okamoto, T. Takane, S. Gohda, Y. Kubozono, K. Sato, M. Yamaji, and K. Satake
    • Journal Title

      Chem. Lett.,

      Volume: 59 Issue: 7 Pages: 994-996

    • DOI

      10.1246/cl.140182

    • NAID

      130004868234

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] ベンゼンクロモフォアを持つシクロファンの光反応2014

    • Author(s)
      岡本秀毅
    • Journal Title

      光化学

      Volume: 45 Pages: 2-8

    • NAID

      40020083584

    • Related Report
      2013 Research-status Report
  • [Journal Article] Fabrication of high performance / highly functional field-effect transistor devices based on [6]phenacene thin films2013

    • Author(s)
      Ritsuko Eguchi, Xuexia He, Shino Hamao, Hidenori Goto, Hideki Okamoto, Shin Gohda, Kaori Sato and Yoshihiro Kubozono
    • Journal Title

      Phys. Chem. Chem. Phys

      Volume: 15 Issue: 47 Pages: 20611-20611

    • DOI

      10.1039/c3cp53598c

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] S2 fluorescence from picene vapor2013

    • Author(s)
      T. Itoh, M. Yamaji, H. Okamoto
    • Journal Title

      Chemical Physics Letters

      Volume: 印刷中 Pages: 26-28

    • DOI

      10.1016/j.cplett.2013.03.055

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] フロー法によるMallory光環化反応の効率化と置換ピセンの合成への展開2015

    • Author(s)
      高根貴光,岡本秀毅
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学船橋キャンパス(船橋)
    • Year and Date
      2015-03-25 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] ベンゼンおよびナフタレンをコアに持つアザシクロファンの合成2015

    • Author(s)
      山本昌典,岡本秀毅
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学船橋キャンパス(船橋)
    • Year and Date
      2015-03-25 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthesis of Phenacenes by Photochemical Cyclization Reactions of Diarylethanes and Diarylethenes2014

    • Author(s)
      Hideki Okamoto and Minoru Yamaji
    • Organizer
      The 8th Taiwan-Japan Bilateral Symposium on Architecture of Functional Organic Molecules
    • Place of Presentation
      Convention Bureau, Memorial Auditorium, Kyushu University
    • Year and Date
      2014-11-27 – 2014-11-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] Photophysical and Photochemical Processes of Excited Singlet and Triplet [3n]Cyclophanes (n = 2–6) Studied by Emission Measurements, Steady-state and Laser Flash Photolyses2014

    • Author(s)
      Minoru Yamaji, Hideki Okamoto and Teruo Shinmyozu
    • Organizer
      The 8th Taiwan-Japan Bilateral Symposium on Architecture of Functional Organic Molecules
    • Place of Presentation
      Convention Bureau, Memorial Auditorium, Kyushu University
    • Year and Date
      2014-11-27 – 2014-11-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 光環化反応によるフェナセンの合成と高性能OFETへの展開2014

    • Author(s)
      岡本秀毅
    • Organizer
      大阪府立大学21世紀科学研究機構分子エレクトロニックデバイス研究所第16回研究会
    • Place of Presentation
      大阪府立大学(堺)
    • Year and Date
      2014-11-25
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 光でつくるフェナセン:合成と電子材料への展開2014

    • Author(s)
      岡本秀毅
    • Organizer
      第15回日本写真学会アンビエント技術研究会
    • Place of Presentation
      東京工芸大学中野キャンパス(東京)
    • Year and Date
      2014-10-16
    • Related Report
      2014 Annual Research Report
  • [Presentation] 光縮環法を用いたアシルフェナセンの合成と光物理・光化学的性質の研究2014

    • Author(s)
      久保田知朗,岡本秀毅,山路 稔
    • Organizer
      2014年光化学討論会
    • Place of Presentation
      北海道大学(札幌)
    • Year and Date
      2014-10-11 – 2014-10-13
    • Related Report
      2014 Annual Research Report
  • [Presentation] ジアザパラシクロファンの光化学反応におけるベンゼンの二量化反応2014

    • Author(s)
      岡本秀毅,岡林善司,新名主輝男,佐竹 恭介
    • Organizer
      2014年光化学討論会
    • Place of Presentation
      北海道大学(札幌)
    • Year and Date
      2014-10-11 – 2014-10-13
    • Related Report
      2014 Annual Research Report
  • [Presentation] Efficient Synthetic Flow Photoreaction: Facile Preparation of Phenacenes and Their Application to OFET2014

    • Author(s)
      Hideki Okamoto, Takamitsu Takane, Shin Gohda, Minoru Yamaji, and Yoshihiro Kubozono
    • Organizer
      The 10th Korea-Japan Symposium on Frontier Photoscience 2014 (KJFP2014)
    • Place of Presentation
      Ewha Womens University, Seoul, Korea
    • Year and Date
      2014-06-21 – 2014-06-23
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Synthesis of Phenacenes by Mallory Reaction: Comparison of Efficiencies by Batch and Flow Photolyses2014

    • Author(s)
      Takamitsu Takane and Hideki Okamoto
    • Organizer
      The 10th Korea-Japan Symposium on Frontier Photoscience 2014 (KJFP2014)
    • Place of Presentation
      Ewha Womens University, Seoul, Korea
    • Year and Date
      2014-06-21 – 2014-06-23
    • Related Report
      2014 Annual Research Report
  • [Presentation] Photochemical synthesis of [n]phenacenes: 9-fluorenone sensitized photocyclization of 1,2-diarylethane2013

    • Author(s)
      Hideki Okamoto, Minoru Yamaji, Shin Gohda, Yoshihiro Kubozono and Kyosuke Satake
    • Organizer
      The 9th Korea-Japan Symposium on Frontier Photoscience – 2013
    • Place of Presentation
      Seoul National University
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] ベンゼン環上にフッ素置換基を持つジアザパラシクロファンの光化学反応2013

    • Author(s)
      岡本秀毅,香西徹哉,新名主輝男,佐竹恭介
    • Organizer
      2013年光化学討論会
    • Place of Presentation
      松山
    • Related Report
      2013 Research-status Report
  • [Presentation] Mallory環化によるフェナセンの合成:光フローリアクタを用いる合成の効率化2013

    • Author(s)
      岡本秀毅,郷田 慎,柴田明奈,佐藤かおり,山路 稔,佐竹 恭介
    • Organizer
      2013年光化学討論会
    • Place of Presentation
      松山
    • Related Report
      2013 Research-status Report
  • [Presentation] フッ素置換アザシクロファンの光化学反応によるカゴ型ジエン生成とその構造及び反応性2013

    • Author(s)
      岡本秀毅,香西徹哉,岡林善司,新名主輝男,佐竹恭介
    • Organizer
      013年日本化学会中国四国支部大会
    • Place of Presentation
      東広島
    • Related Report
      2013 Research-status Report
  • [Presentation] Photoreaction of Fluorinated 2,11-Diaza[3.3]paracyclophane: Formation of Cage Diene Type Benzene Dimer2013

    • Author(s)
      Hideki Okamoto, Tetsuya Kozai and Kyosuke Satake
    • Organizer
      The 9th Korea-Japan Symposium on Frontier Photoscience–2013 (KJFP2013), Seoul National University, Seoul, Korea, November 24-27, 2013
    • Place of Presentation
      Seoul National University
    • Related Report
      2013 Research-status Report
  • [Presentation] ベンゼン環上にフッ素原子を導入したジアザ[3.3]パラシクロファンの合成と光化学反応2013

    • Author(s)
      岡本秀毅,香西徹哉,岡林善司,新名主輝男,佐竹恭介
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津
    • Related Report
      2012 Research-status Report
  • [Presentation] 2,11-ジアザ[3.3]パラシクロファンの光化学反応:p,p’-ジベンゼン骨格の生成2012

    • Author(s)
      岡本秀毅,岡林善司,上原広之,伊藤 慧,新名主輝男,佐竹恭介
    • Organizer
      2012年光化学討論会
    • Place of Presentation
      東京工業大学(東京)
    • Related Report
      2012 Research-status Report
  • [Presentation] ジアザ[3.3]パラシクロファンの合成,構造および光化学反応2012

    • Author(s)
      岡本秀毅,岡林善司,上原広之,伊藤 慧,新名主輝男,佐竹恭介
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都テルサ(京都)
    • Related Report
      2012 Research-status Report
  • [Presentation] 光化学反応によるフルミネン([6]フェナセン)の合成および電子スペクトル2012

    • Author(s)
      岡本秀毅,山路稔,郷田慎,佐藤かおり,杉野久子,佐竹恭介
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都テルサ(京都)
    • Related Report
      2012 Research-status Report
  • [Presentation] ベンゼン環上に置換基を有する 2,11-ジアザ[3.3]パラシクロファン誘導体の合成2012

    • Author(s)
      岡本秀毅,香西徹哉,岡林善司,佐竹恭介
    • Organizer
      2012年日本化学会西日本大会
    • Place of Presentation
      佐賀大学(佐賀)
    • Related Report
      2012 Research-status Report
  • [Presentation] 3,10-ピセンジカルボン酸エステルの簡便な合成2012

    • Author(s)
      岡本秀毅,寺門辰哉,佐竹恭介
    • Organizer
      2012年日本化学会西日本大会
    • Place of Presentation
      佐賀大学(佐賀)
    • Related Report
      2012 Research-status Report
  • [Presentation] Photochemical Synthesis and Properties of [n]Phenacenes (n= 3–6)2012

    • Author(s)
      M. Yamaji, H. Okamoto
    • Organizer
      7th Asian Photochemistry Conference 2012 (APC2012)
    • Place of Presentation
      Osaka University (Suita)
    • Related Report
      2012 Research-status Report
  • [Presentation] 有機電子材料の合成:光反応を利用するフェナセンの簡便な合成法の開発

    • Author(s)
      岡本秀毅
    • Organizer
      岡山大学知恵の見本市2012
    • Place of Presentation
      岡山大学(岡山)
    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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