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Synthesis of novel nitrogen-containing macrocycles incorporating anthracene units, and elucidation of their redox behavior

Research Project

Project/Area Number 16K17874
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionOkayama University of Science

Principal Investigator

Iwanaga Tetsuo  岡山理科大学, 理学部, 准教授 (40454805)

Research Collaborator WAKAMATSU Kan  
Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2018: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2017: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywordsアントラセン / カルバゾール / 含窒素大環状化合物 / クロスカップリング / パイ共役系 / 酸化還元挙動 / 電子スペクトル / 電解吸収スペクトル / 電気化学的性質 / 分光学的性質 / 大環状化合物 / パイ電子系 / 光特性 / 酸化還元
Outline of Final Research Achievements

The rigid macrocyclic compounds incorporating electron-rich pi-electron units exhibit interesting electronic properties and oxidation behaviors. In this study, we have developed the efficient synthesis of nitrogen-containing macrocycles and elucidated their redox behavior. We succeeded in the synthesis of the various macrocycles that differed in substitution positions of the anthrylene unit linked by nitrogen, and the electronic properties of the oxidized species were determined by the electronic spectra and DFT calculation. In particular, the nitrogen-containing macrocycles incorporating 9,10-anthrylene units exhibited specific electronic properties due to their structural factors. We have established the novel macrocyclic molecular design utilizing the structural features of anthracene.

Academic Significance and Societal Importance of the Research Achievements

本研究で開発した含窒素大環状分子は,適切な置換位置で連結したアントラセン骨格を組み込むことで新奇な電子構造を発現することを見出した.アントラセン骨格の構造的な効果に基づく分子設計は,これまで主流であったパイ電子系の拡張による電子物性の発現とは異なり,従来にないアントラセン骨格の利用法として新しい分子構造と電子物性を引き出すことができた.今後,これらの分子設計指針を利用することで電子豊富な分子系の構築とそれらを利用した電荷とスピンを制御・利用するスピンエレクトロニクス分野や高いドナー性を利用した正孔輸送材料など有機機能性材料の開発などへ大きな波及効果があると考えられる.

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (37 results)

All 2019 2018 2017 2016 Other

All Int'l Joint Research (1 results) Journal Article (11 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 11 results,  Acknowledgement Compliant: 3 results) Presentation (22 results) (of which Int'l Joint Research: 3 results,  Invited: 3 results) Remarks (3 results)

  • [Int'l Joint Research] Friedrich-Alexander University(ドイツ)

    • Related Report
      2016 Research-status Report
  • [Journal Article] Synthesis and Photophysical Properties of Dinaphto[2,3-b:2',3'-i]dihydrophenazine Derivatives2019

    • Author(s)
      Tetsuo Iwanaga, Naoto Asano, Haruo Yamada, Shinji Toyota
    • Journal Title

      Tetrahedron Letters

      Volume: 60 Issue: 16 Pages: 1113-1116

    • DOI

      10.1016/j.tetlet.2019.03.035

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Saddle-shaped Macrocycle Comprising 2,5-Diphenylthiophene Units2018

    • Author(s)
      Iwanaga Tetsuo、Yamada Yuki、Yamauchi Tomokazu、Misaki Yohji、Inoue Masataka、Yamada Haruo
    • Journal Title

      Chemistry Letters

      Volume: 47 Issue: 6 Pages: 760-762

    • DOI

      10.1246/cl.180187

    • NAID

      130007384495

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Electronic Properties of Length-Defined 9,10-Anthrylene-Butadiynylene Oligomers2018

    • Author(s)
      Nagaoka Maiko、Tsurumaki Eiji、Nishiuchi Mai、Iwanaga Tetsuo、Toyota Shinji
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 印刷中 Issue: 10 Pages: 5784-5790

    • DOI

      10.1021/acs.joc.8b00311

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Conformational Analysis of 10-Mesitylanthracene-1,8-diyl Oligomers2018

    • Author(s)
      Shinji Toyota, Toyoaki Saibara, Kei Fujise, Tomohiro Oki, Tetsuo Iwanaga
    • Journal Title

      Synlett

      Volume: 29 Issue: 16 Pages: 2137-2140

    • DOI

      10.1055/s-0037-1609869

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Inclusion of Chlorinated Hydrocarbon Guests by 9,9’-Bianthracene Host and its Selectivity2018

    • Author(s)
      Shinji Toyota, Aya Yokoyama, Kunihiko Tanaka, Yusuke Akaki, Tetsuo Iwanaga
    • Journal Title

      Journal of Inclusion Phenomena and Macrocyclic Chemistry

      Volume: 92 Issue: 1-2 Pages: 129-136

    • DOI

      10.1007/s10847-018-0821-1

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] An Isolable Triradical Trication of Hexaaza[16]paracyclophane with Embedded 9,10-Anthrylenes: A Frustrated 3-Spin Systems2017

    • Author(s)
      R. Kurata, D. Sakamaki, M. Uebe, M. Kinoshita, T. Iwanaga, T. Matsumoto, A. Ito
    • Journal Title

      Organic Letters

      Volume: 19 Issue: 16 Pages: 4371-4374

    • DOI

      10.1021/acs.orglett.7b02088

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Oxidation State-Dependent Intramolecular Electronic Interaction of Carbazole-Based Azacyclophanes with 9,10-Anthrylene Units2017

    • Author(s)
      Iwanaga Tetsuo、Yamauchi Tomokazu、Toyota Shinji、Suzuki Shuichi、Okada Keiji
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 82 Issue: 19 Pages: 10699-10703

    • DOI

      10.1021/acs.joc.7b01688

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis, structures, and properties of 2,5-dianthrylthiophene derivatives2017

    • Author(s)
      S. Toyota, M. Nishiuchi, T. Iwata, T. Yamauchi, T. Iwanaga, M. Hasegawa
    • Journal Title

      Can. J. Chem.

      Volume: 95 Issue: 3 Pages: 286-291

    • DOI

      10.1139/cjc-2016-0391

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 1,8-anthracene-ethenylene cyclic dimers and related compounds: effects of linkers on their structures, electronic properties, and dynamic behavior2017

    • Author(s)
      M. Inoue, T. Iwanaga, S. Toyota
    • Journal Title

      Asian J. Org. Chem.

      Volume: 印刷中 Issue: 5 Pages: 566-574

    • DOI

      10.1002/ajoc.201700046

    • Related Report
      2017 Research-status Report 2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Triple and Quadruple Triptycene Gears in Rigid Macrocyclic Frameworks2017

    • Author(s)
      S. Toyota, K. Kawahata, K. Sugahara, K. Wakamatsu, T. Iwanaga
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2017 Issue: 37 Pages: 5696-5707

    • DOI

      10.1002/ejoc.201701067

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Planar Anthracene-Acetylene Frameworks as Stereogenic Motif2017

    • Author(s)
      S. Toyta, H. Ikeda, T. Iwanaga
    • Journal Title

      ChemPlusChem

      Volume: 印刷中 Issue: 7 Pages: 957-966

    • DOI

      10.1002/cplu.201600646

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Presentation] ジエチニルアセン類を組み込んだパイ拡張型アントラセンビスイミド誘導体の合成と分光学的性質2019

    • Author(s)
      石川天太,N. Johannes,R. R. Tykwinski,岩永哲夫
    • Organizer
      日本化学会第99春季年会(2019)
    • Related Report
      2018 Annual Research Report
  • [Presentation] 2,7-アントリレンユニットとフェニレンジアミンを組み込んだ含窒素大環状分子の合成と物性2019

    • Author(s)
      小森隆史,山内智和,御崎洋二,岩永哲夫
    • Organizer
      日本化学会第99春季年会(2019)
    • Related Report
      2018 Annual Research Report
  • [Presentation] Construction of donor-acceptor arrays based on anthracene units2018

    • Author(s)
      Tetsuo Iwanaga
    • Organizer
      Bilateral Join Workshop on Photofunctional Materials between Sungkyunkwan University and Okayama University
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and Photophysical Properties of Azacyclophanes Incorporating Anthracene Units.2018

    • Author(s)
      Tetsuo Iwanaga, Tomokazu Yamauchi, Shinji Toyota
    • Organizer
      14th International Kyoto Conference on New Aspects Organic Chemistry
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] トリフェニルアミン基盤大環状化合物の合成とペロブスカイト型太陽電池における正孔輸送材料としての応用2018

    • Author(s)
      小森隆史,嶋崎愛,若宮淳志,岩永哲夫
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 2,3-置換アントラキノンを基盤としたドナー/アクセプター型分子の合成と分光学的性質2018

    • Author(s)
      浅野直人,池田一登,高橋広奈,酒井誠,岩永哲夫
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 9,10-ジエチニルアントラセンを組み込んだアントラセンビスイミド誘導体の合成と分光学2018

    • Author(s)
      石川天太,山田晴夫,岩永哲夫
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] ヘキサアザ(4,4')ビフェニロファン誘導体の合成と電気化学的性質2018

    • Author(s)
      小森隆史,岩永哲夫
    • Organizer
      第12回有機π電子系シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] 多様な位置で縮環したカルバゾール二量体の合成と分光学的性質2018

    • Author(s)
      沖朋弘,守岡義弘,岩永哲夫
    • Organizer
      第12回有機π電子系シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] ユニークな電子構造を有する剛直な含窒素大環状化合物の合成と応用2018

    • Author(s)
      岩永哲夫
    • Organizer
      日本化学会中国四国支部「固体物性化学の最前線」講演会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] アントラセンユニットを組み込んだ含窒素大環状化合物の合成と物性2018

    • Author(s)
      岩永哲夫,山内智和,小森隆史,鈴木修一,豊田真司,嶋崎愛,若宮淳志,村田靖次郎
    • Organizer
      日本化学会第98春季年会(2018)
    • Related Report
      2017 Research-status Report
  • [Presentation] カルバゾールを基盤とした含窒素大環状化合物の合成と物性2017

    • Author(s)
      山内智和,岩永哲夫,鈴木修一,岡田惠次,豊田真司
    • Organizer
      日本化学会第97春季年会(2017)
    • Place of Presentation
      慶應義塾大学(神奈川)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] Synthesis and Electrochemical Properties of Carbazole-Based Azacyclophanes with Anthracene Units.2017

    • Author(s)
      T. Iwanaga, T. Yamauchi, S. Toyota, S. Suzuki, K. Okada
    • Organizer
      17th International Symposium on Novel Aromatic Compounds
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] ユニークな電子構造を有する含窒素パイ共役分子の創製2017

    • Author(s)
      岩永哲夫
    • Organizer
      構造有機化学若手研究者・研究会2017
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] カルバゾールとアントラセンユニットを連結した含窒素大環状化合物の合成と電子的性質2017

    • Author(s)
      岩永哲夫,山内智和,豊田真司,鈴木修一,岡田惠次
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 2,7-アントリレンを組み込んだ含窒素大環状化合物の合成と電気化学的性質2017

    • Author(s)
      小森隆史,岩永哲夫,豊田真司
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] Dinaphtho[b,i]phenazine誘導体の合成と分光学的性質2017

    • Author(s)
      浅野直人,山田晴夫,岩永哲夫
    • Organizer
      第11回有機π電子系シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] アセンユニットを基盤とした大環状のオリゴマーの合成研究2017

    • Author(s)
      大塚純也,山田晴夫,岩永哲夫
    • Organizer
      第11回有機π電子系シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] 2,7-アントリレンユニットを基盤とした含窒素大環状化合物の合成と分光学的性質2017

    • Author(s)
      小森隆史,岩永哲夫,豊田真司
    • Organizer
      第11回有機π電子系シンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] カルバゾールとアントラセンユニットを連結した含窒素大環状化合物の合成と分光学的性質2016

    • Author(s)
      岩永哲夫,山内智和,豊田真司,鈴木修一,岡田惠次
    • Organizer
      第10回有機π電子系シンポジウム
    • Place of Presentation
      あうる京北(京都)
    • Year and Date
      2016-12-16
    • Related Report
      2016 Research-status Report
  • [Presentation] カルバゾールユニットを基盤とした含窒素大環状化合物の合成と酸化状態における電子的性質2016

    • Author(s)
      山内智和,岩永哲夫,豊田真司,鈴木修一,岡田惠次
    • Organizer
      第10回有機π電子系シンポジウム
    • Place of Presentation
      あうる京北
    • Year and Date
      2016-12-16
    • Related Report
      2016 Research-status Report
  • [Presentation] カルバゾールユニットで構成された含窒素大環状化合物の合成と電気化学的性質2016

    • Author(s)
      山内智和,岩永哲夫,豊田真司,鈴木修一,岡田惠次
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島国際会議場(広島)
    • Year and Date
      2016-09-01
    • Related Report
      2016 Research-status Report
  • [Remarks] 岡山理科大学・理学部化学科・物理有機化学研究室HP

    • URL

      http://butuyu2.chem.ous.ac.jp

    • Related Report
      2018 Annual Research Report
  • [Remarks] 岡山理科大学・物理有機化学研究室HP

    • URL

      http://butuyu2.chem.ous.ac.jp

    • Related Report
      2017 Research-status Report
  • [Remarks] 物理有機化学研究室HP

    • URL

      http://butuyu2.chem.ous.ac.jp

    • Related Report
      2016 Research-status Report

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Published: 2016-04-21   Modified: 2020-03-30  

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