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Synthesis of distorted pi conjugated molecules by intermolecular radical reactions

Research Project

Project/Area Number 25410039
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

Hiroto Satoru  名古屋大学, 工学(系)研究科(研究院), 助教 (30547427)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsポルフィリン / π曲面 / ヘリセン / バッキーボウル / フラーレン包接 / キラル誘起 / キラル発光 / フラーレン / キャリア移動度 / 歪み / ねじれ / π共役分子 / 酸化的縮環反応
Outline of Final Research Achievements

Curved-π conjugated molecules have attracted considerable intersts for the potential application to novel molecular devices based on the unique properties originating from the curved-π surface. In this project, we have achieved novel kinds of curved-π molecules with brilliant functions under mild reaction conditions, which are originated in conventional aniline and phenol oxidations. Accordingly, we have succeeded in the synthesis of highly twisted porphyrin oligomers with the largest twisting angle reported before. In addition, we disclosed the high chiral emissive feature of π-extended helicenes based on anthracenes. Finally, we have accomplished the synthesis of nitrogen-embedded buckybowl, which has been impossible to be synthesized under conventional conditions.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (56 results)

All 2016 2015 2014 2013

All Journal Article (17 results) (of which Peer Reviewed: 17 results,  Open Access: 7 results,  Acknowledgement Compliant: 8 results) Presentation (39 results) (of which Int'l Joint Research: 8 results,  Invited: 9 results)

  • [Journal Article] Fully-Substituted 1,3-Butadienes as π-Conjugated Linkers between Pyrenes2016

    • Author(s)
      K. Oda
    • Journal Title

      Chem. Lett.

      Volume: 45 Issue: 4 Pages: 403-405

    • DOI

      10.1246/cl.151181

    • NAID

      130005143982

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] The synthesis of NiII and AlIII 10-azacorroles through coordination-induced cyclisation involving 1,2-migration2016

    • Author(s)
      H. Omori, S. Hiroto, H. Shinokubo
    • Journal Title

      Chemical Communications

      Volume: 52 Issue: 17 Pages: 3540-3542

    • DOI

      10.1039/c5cc10247b

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Control of Conformation and Chirality of Nonplanar π-Conjugated Diporphyrins using Substituents and Axial Ligands2016

    • Author(s)
      S. Ito
    • Journal Title

      Chem. Asian J.

      Volume: 11 Issue: 6 Pages: 936-942

    • DOI

      10.1002/asia.201600105

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Nitrogen-embedded buckybowl and its assembly with C602015

    • Author(s)
      H. Yokoi, Y. Hiraoka, S. Hiroto, D. Sakamaki, S. Seki, H. Shinokubo
    • Journal Title

      Nature Communications

      Volume: 6 Issue: 1 Pages: 8215-8215

    • DOI

      10.1038/ncomms9215

    • NAID

      120005745626

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Indolylindolinone: Easily Accessible, Tunable, and Wide-Range Absorbing Dyes2015

    • Author(s)
      A. Shiegno
    • Journal Title

      Chem. Lett.

      Volume: 44 Issue: 12 Pages: 1703-1705

    • DOI

      10.1246/cl.150815

    • NAID

      130005112551

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Isolation of a 1,4-diketone intermediate in oxidative dimerization of 2-hydroxyanthracene and its conversion to oxahelicene2015

    • Author(s)
      T. Matsuno, Y. Koyama, S. Hiroto, J. Kumar, T. Kawai H. Shinokubo
    • Journal Title

      Chemical Communications

      Volume: 51 Issue: 22 Pages: 4607-4610

    • DOI

      10.1039/c5cc00764j

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Macrocyclic dipyrrin dimer bridged by ethylene and dioxyphenylene linkers2015

    • Author(s)
      J.-Y. Shin, S. Hiroto, H. Shinokubo
    • Journal Title

      J. Porphyrins Phthalocyanines

      Volume: 19 Issue: 01-03 Pages: 135-135

    • DOI

      10.1142/s108842461450093x

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] One-Step Reaction that Yields Highly Twisted and Fully π-Conjugated Porphyrinic Oligomers2015

    • Author(s)
      Satoru Ito, Satoru Hiroto, Sangsu Lee, Minjung Son, Ichiro Hisaki, Takuya Yoshida, Dongho Kim, Nagao Kobayashi, Hiroshi Shinokubo
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 137 Issue: 1 Pages: 142-145

    • DOI

      10.1021/ja511905f

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Synthesis, Reactivity, and Property of 5,15-Dithiaporphyrin Copper(II) Complex2014

    • Author(s)
      N. Wachi, T. Kondo, S. Ito, S. Hiroto, J.-Y. Shin, H. Shinokubo
    • Journal Title

      J. Porphyrins Phthalocyanines

      Volume: 18 Issue: 08n09 Pages: 675-678

    • DOI

      10.1142/s1088424614500412

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Synthesis of Curved Hexa-peri-hexabenzocoronenes2014

    • Author(s)
      Ryuichi Yamaguchi, Satoru Hiroto, Hiroshi Shinokubo
    • Journal Title

      Chemistry Letters

      Volume: 43 Issue: 10 Pages: 1637-1639

    • DOI

      10.1246/cl.140577

    • NAID

      130004693827

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Regioselective Double Cyclization of 5,15-Bis(trimethylsilylethynyl)porphyrin to Provide Di(oxoethano)porphyrin2014

    • Author(s)
      K. Oda, S. Hiroto, H. Shinokubo
    • Journal Title

      Chem. Lett.

      Volume: 43 Issue: 9 Pages: 1444-1446

    • DOI

      10.1246/cl.140470

    • NAID

      130004427172

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Diazo-Bridged BODIPY Dimer and Tetramer by Oxidative Coupling of beta-Amino-Substituted BODIPYs2014

    • Author(s)
      H. Yokoi, S. Hiroto, and H. Shinokubo
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 11 Pages: 3004-3007

    • DOI

      10.1021/ol501131j

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Facile Synthesis of Nitrogen-Containing Polycyclic Aromatic Hydrocarbons from Perylene Bisimides2014

    • Author(s)
      S. Ito, S. Hiroto, H. Shinokubo
    • Journal Title

      Chem. Lett.

      Volume: 43 Pages: 1309-1311

    • NAID

      130004677580

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Silylethynyl Substituents as Porphyrin Protecting Groups for Solubilization and Selectivity Control K. Oda, M. Akita, S.2014

    • Author(s)
      K. Oda
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 6 Pages: 1818-1821

    • DOI

      10.1021/ol500569b

    • Related Report
      2014 Research-status Report 2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Near-IR Absorbing Nickel(II) Porphyrinoids Prepared by Regioselective Insertion of Silylenes into Antiaromatic Nickel(II) Norcorrole2014

    • Author(s)
      Takaki Fukuoka, Kenya Uchida, Young Mo Sung, Ji-Young Shin, Shintaro Ishida, Dr. Jong Min Lim, Satoru Hiroto, Ko Furukawa, Dongho Kim, Takeaki Iwamoto, Hiroshi Shinokubo
    • Journal Title

      Angewandte Chemie, International Edition

      Volume: 53 Issue: 6 Pages: 1506-1509

    • DOI

      10.1002/anie.201309921

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Oxidation of 2-amino-substituted BODIPYs providing pyrazine-fused BODIPY trimers2014

    • Author(s)
      H. Yokoi
    • Journal Title

      Chem. Commun.

      Volume: 50 Issue: 21 Pages: 2715-2717

    • DOI

      10.1039/c3cc48738e

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Pyridine-Fused Perylene Imides with an Amidine Moiety for Hydrogen Bonding2013

    • Author(s)
      S. Ito
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 12 Pages: 3110-3113

    • DOI

      10.1021/ol401316q

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 中心に窒素原子をもつバッキーボウルの物性とフラーレン包接挙動2016

    • Author(s)
      横井 寛生・平岡 勇哉・廣戸 聡・酒巻 大輔・関 修平・忍久保 洋
    • Organizer
      日本化学会 第96春季年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 二次元π共役分子を素材とした新規機能性曲面構造の創出2016

    • Author(s)
      廣戸 聡
    • Organizer
      超分子創製化学セミナー
    • Place of Presentation
      立命館大学
    • Year and Date
      2016-02-29
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] The synthesis of novel π-conjugated molecules with highly distorted surface2016

    • Author(s)
      Satoru Hiroto
    • Organizer
      ad hoc seminar
    • Place of Presentation
      University of Arizona
    • Year and Date
      2016-01-07
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Straightforward synthesis of highly twisted porphyrin oligomers2015

    • Author(s)
      Satoru Hiroto, Satoru Ito, Hiroshi Shinokubo
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2015-12-17
    • Related Report
      2015 Annual Research Report
  • [Presentation] Creation of novel three-dimensional π-conjugated element blocks with highly curved surface2015

    • Author(s)
      Satoru Hiroto
    • Organizer
      PPC-14
    • Place of Presentation
      Kauai, USA
    • Year and Date
      2015-12-07
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Creation of novel three-dimensional π-conjugated element blocks with highly curved surface2015

    • Author(s)
      Satoru Hiroto
    • Organizer
      Mini-symposium
    • Place of Presentation
      VCU
    • Year and Date
      2015-10-26
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 中心に窒素原子をもつバッキーボウルの合成と物性の解明2015

    • Author(s)
      横井寛生・平岡勇哉・廣戸聡・酒巻大輔・関修平・忍久保洋
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛大学
    • Year and Date
      2015-09-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] ヒドロキシテトラセンの酸化を用いたオキサヘリセンの合成2015

    • Author(s)
      松野崇志・廣戸聡・忍久保洋
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛大学
    • Year and Date
      2015-09-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] アザヘリセンを基盤としたキラル8の字型分子の合成2015

    • Author(s)
      牛山 綾子、廣戸 聡、忍久保 洋
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛大学
    • Year and Date
      2015-09-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Straightforward Synthesis of Highly Twisted Porphyrin Oligomers2015

    • Author(s)
      Satoru Hiroto, Satoru Ito, Hiroshi Shinokubo
    • Organizer
      250th ACS Meeting
    • Place of Presentation
      Boston, USA
    • Year and Date
      2015-08-19
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Highly Distorted π-Surfaces by Oxidation of Functional Molecules2015

    • Author(s)
      Satoru Hiroto, Hiroshi Shinokubo
    • Organizer
      ISNA-16
    • Place of Presentation
      Madrid, Spain
    • Year and Date
      2015-07-09
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Highly Distorted π-Conjugated Functional Molecules2015

    • Author(s)
      Satoru Hiroto, Hiroshi Shinokubo
    • Organizer
      8th International Conference on Materials for Advanced Technologies of the Materials Research Society of Singapore
    • Place of Presentation
      Singapore
    • Year and Date
      2015-07-01
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 新規π拡張ジヒドロフェナジン誘導体の合成2015

    • Author(s)
      横井寛生・廣戸聡・忍久保洋
    • Organizer
      第2回π造形化学公開シンポジウム
    • Place of Presentation
      大阪市中央公会堂
    • Year and Date
      2015-06-08
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Regioselective direct functionalization of antiaromatic norcorrole2015

    • Author(s)
      Ryo Nozawa, Ji-Young Shin, Hiroto Satoru, Hiroshi Shinokubo
    • Organizer
      第2回π造形化学公開シンポジウム
    • Place of Presentation
      大阪市中央公会堂
    • Year and Date
      2015-06-08
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 歪んだπ平面の新規構築法: 酸化反応による迅速合成2015

    • Author(s)
      廣戸 聡
    • Organizer
      CNSセミナー
    • Place of Presentation
      九州大学
    • Year and Date
      2015-06-05
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 高度にねじれたポルフィリン多量体の合成2015

    • Author(s)
      廣戸 聡、伊藤 覚、忍久保 洋
    • Organizer
      第69回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      横浜国立大学
    • Year and Date
      2015-05-16
    • Related Report
      2015 Annual Research Report
  • [Presentation] アニリンやフェノールの酸化反応をベースとした高歪π共役分子の合成2015

    • Author(s)
      廣戸聡
    • Organizer
      第95回日本化学会春季年会
    • Place of Presentation
      日本大学船橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] Straightforward Approach to 3D π-conjugated Molecules from 2D π-conjugated System2014

    • Author(s)
      Satoru Hiroto
    • Organizer
      8th Singapore international Chemistry Conference, Singapore
    • Place of Presentation
      Singapore
    • Year and Date
      2014-12-15 – 2014-12-20
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] Room-temperature Synthesis of Highly-Twisted Porphyrin Oligomers2014

    • Author(s)
      Satoru Hiroto, Satoru Ito, Hiroshi Shinokubo
    • Organizer
      the 9th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      Malaysia
    • Year and Date
      2014-12-01 – 2014-12-05
    • Related Report
      2014 Research-status Report
  • [Presentation] π共役分子をねじる:ビラジカルからの出発2014

    • Author(s)
      廣戸聡
    • Organizer
      第1回π造形若手研究会
    • Place of Presentation
      熱海
    • Year and Date
      2014-11-22 – 2014-11-23
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] Synthesis of oxa[7]helicenes as a highly emissive helical-shaped molecule2014

    • Author(s)
      Satoru Hiroto, Yutaro Koyama, Takashi Matsuno, Tsuyoshi Kawai, Hiroshi Shinokubo
    • Organizer
      International Symposium on the Synthesis and Application of Curved Organic π-molecules and Materials
    • Place of Presentation
      京都大学宇治キャンパス
    • Year and Date
      2014-10-21 – 2014-10-22
    • Related Report
      2014 Research-status Report
  • [Presentation] アニリンの酸化反応を応用したアントラセン縮環多量体の合成2014

    • Author(s)
      廣戸 聡、後藤 澄光、忍久保 洋
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学川内キャンパス
    • Year and Date
      2014-09-08 – 2014-09-10
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthesis of Porphyrin Analogues with Indole Units and Their Metal Complexes2014

    • Author(s)
      Satoru Hiroto, Ami Shigeno, Hiroshi Shinokubo
    • Organizer
      8th International Symposium on Porphyrins and Phthalocyanines
    • Place of Presentation
      Turkey
    • Year and Date
      2014-06-22 – 2014-06-27
    • Related Report
      2014 Research-status Report
  • [Presentation] 高度な歪みを有するπ共役分子合成法の開発2014

    • Author(s)
      廣戸聡
    • Organizer
      大阪大学関研究室
    • Place of Presentation
      大阪大学吹田キャンパス
    • Year and Date
      2014-06-18
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] ヘキサベンゾコロネンテトラオンの修飾反応2014

    • Author(s)
      山口 龍一,廣戸 聡,忍久保 洋
    • Organizer
      第94回日本化学会春季年会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] ピレン含有π共役オリゴエンの合成と物性2014

    • Author(s)
      小田 一磨,廣戸 聡,忍久保 洋
    • Organizer
      第94回日本化学会春季年会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] アルキニル基の水和を利用したメゾ-β縮環型ポルフィリンの合成2014

    • Author(s)
      小田 一磨,廣戸 聡,忍久保 洋
    • Organizer
      第94回日本化学会春季年会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] 窒素架橋ジピリン誘導体を用いたアザコロールの新規合成法2014

    • Author(s)
      大森 裕土,廣戸 聡,忍久保 洋
    • Organizer
      第94回日本化学会春季年会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] フェナントレン誘導体の酸化による歪んだ二量体の合成2014

    • Author(s)
      横井 寛生,廣戸 聡,忍久保 洋
    • Organizer
      第94回日本化学会春季年会
    • Place of Presentation
      名古屋大学東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] アントラセンの酸化反応による π拡張ピラジン・ピロールおよびフランの合成2013

    • Author(s)
      廣戸 聡,後藤 澄光,小山 祐太朗,忍久保 洋
    • Organizer
      第43回複素環化学討論会
    • Place of Presentation
      長良川国際会議場
    • Related Report
      2013 Research-status Report
  • [Presentation] ピレン含有共役オリゴエンの合成と構造2013

    • Author(s)
      廣戸 聡,小田 一磨,忍久保 洋
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Research-status Report
  • [Presentation] アルキニル基の水和を用いた新規ポルフィリン化合物の合成2013

    • Author(s)
      小田 一磨,廣戸 聡,忍久保 洋
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Research-status Report
  • [Presentation] フェナントレンの酸化による新規縮環二量体の合成2013

    • Author(s)
      横井 寛生,廣戸 聡,忍久保 洋
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Research-status Report
  • [Presentation] ねじれたπ平面を持つピラジン縮環ポルフィリン二量体の合成2013

    • Author(s)
      伊藤 覚,廣戸 聡,忍久保 洋
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Research-status Report
  • [Presentation] ねじれたπ平面を持つピラジン縮環ポルフィリン二量体の合成2013

    • Author(s)
      伊藤 覚,廣戸 聡,忍久保 洋
    • Organizer
      第3回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀
    • Related Report
      2013 Research-status Report
  • [Presentation] インドール-インドリノンの簡便な合成法の開発とその金属錯体に関する研究2013

    • Author(s)
      滋野 亜美,廣戸 聡,忍久保 洋
    • Organizer
      第43回複素環化学討論会
    • Place of Presentation
      長良川国際会議場
    • Related Report
      2013 Research-status Report
  • [Presentation] β 位にアミノ基を導入した BODIPY の酸化による様々な BODIPY オリゴマーの合成2013

    • Author(s)
      横井 寛生,和智 成彦,廣戸 聡,忍久保 洋
    • Organizer
      第43回複素環化学討論会
    • Place of Presentation
      長良川国際会議場
    • Related Report
      2013 Research-status Report
  • [Presentation] アルキニル基の水和を利用したポルフィリンの新規修飾法の開発2013

    • Author(s)
      小田 一磨,廣戸 聡,忍久保 洋
    • Organizer
      第44回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      静岡大学浜松キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] β–アミノポルフィリンの酸化によるねじれたπ平面を持つ二量体の合成2013

    • Author(s)
      伊藤 覚,廣戸 聡,忍久保 洋
    • Organizer
      第44回中部化学関係学協会支部連合秋季大会
    • Place of Presentation
      静岡大学浜松キャンパス
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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