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Synthesis of Heterographenes via Tandem Hetero-Friedel-Crafts Reactions

Research Project

Project/Area Number 23685020
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionKwansei Gakuin University (2013)
Kyoto University (2011-2012)

Principal Investigator

HATAKEYAMA Takuji  関西学院大学, 理工学部, 准教授 (90432319)

Project Period (FY) 2011-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥29,250,000 (Direct Cost: ¥22,500,000、Indirect Cost: ¥6,750,000)
Fiscal Year 2013: ¥8,450,000 (Direct Cost: ¥6,500,000、Indirect Cost: ¥1,950,000)
Fiscal Year 2012: ¥8,450,000 (Direct Cost: ¥6,500,000、Indirect Cost: ¥1,950,000)
Fiscal Year 2011: ¥12,350,000 (Direct Cost: ¥9,500,000、Indirect Cost: ¥2,850,000)
Keywordsグラフェン / π共役化合物 / フリーデルクラフツ / ヘテロ原子
Research Abstract

We have developed tandem hetero-Friedel Crafts reactions and multiple cross-coupling reactions toward synthesis of heterographene, which attracts the interest of chemists and physicists in recent years. Using these reactions, we have succeeded in short-step synthesis of heteronanographenes, substructure molecules of heterographenes. These molecules showed high charge transport ability and fluorescence property and thus enabled us to fabricate phosphorescent OLED with high efficiency. Heteronanographenes are new and promising materials for organic electronics.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Annual Research Report
  • 2011 Annual Research Report
  • Research Products

    (48 results)

All 2014 2013 2012 2011 Other

All Journal Article (12 results) (of which Peer Reviewed: 12 results) Presentation (26 results) (of which Invited: 2 results) Book (1 results) Remarks (1 results) Patent(Industrial Property Rights) (8 results) (of which Overseas: 5 results)

  • [Journal Article] Azaboradibenzo[6]helicene : Carrier Inversion Induced by Helical Homochirality.2014

    • Author(s)
      Hatakeyama, Takuji, Hashimoto, Sigma, Oba Tsuyoshi, Nakamura, Masaharu
    • Journal Title

      Journal of the American Chemical Society

      Volume: 134 Issue: 48 Pages: 19600-19603

    • DOI

      10.1021/ja310372f

    • Related Report
      2013 Final Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] DFT Study of 5-Endo-Trig-Type Cyclization of 3-Alkenoic Acids Using Pd-SPRIX Catalyst : Importance of the Rigid Spiro Framework for Both Selectivity and Reactivity2013

    • Author(s)
      Gabr, R. K.; Hatakeyama, T; Takenaka, K.; Takizawa, S.; Okada, Y.; Nakamura, M.; Sasai, H
    • Journal Title

      Cem. Eur. J

      Volume: 19 Pages: 9518-9525

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] DFT Study on 5-Endo-Trig-Type Cyclization of 3-Alkenoic Acids Using Pd-SPRIX Catalyst: Importance of the Rigid Spiro Framework for Both Selectivity and Reactivity2013

    • Author(s)
      Gabr, R. K. M.; Hatakeyama, T.; Takenaka, K.; Takizawa, S.; Okada, Y.; Nakamura, M.; Sasai, H.
    • Journal Title

      Chem. Eur. J

      Volume: (in press) Issue: 29 Pages: 9518-9525

    • DOI

      10.1002/chem.201203189

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed Aromatic Amination for Nonsymmetrical Triarylamine Synthesis2012

    • Author(s)
      Takuji, Hatakeyama, Ryuji Imayoshi, Yuya Yoshimoto, Sujit K. Ghorai, Masayoshi Jin, Hikaru Takaya, Kazuhiro Norisue, Yoshiki Sohrin, Masahru Nakamura
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 134 Issue: 50 Pages: 20262-20265

    • DOI

      10.1021/ja309845k

    • Related Report
      2013 Final Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Iron-Catalyzed Alkyl-Alkyl Suzuki -Miyaura Coupling2012

    • Author(s)
      Hatakeyama, T.; Hashimoto, T.; Kathriarachchi, K. K. A. D. S.; Zenmyo, T.; Seike, H.; Nakamura, M
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 51 Issue: 31 Pages: 10674-10676

    • DOI

      10.1021/ja103973a

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Cross-Coupling of Non-activated Chloroalkanes with Aryl Grignard Reagents in the Presence of Iron/N-Heterocyclic Carbene Catalysts2012

    • Author(s)
      Ghorai, S.K.; Jin, M.; Hatakeyama, T.; Nakamura, M.
    • Journal Title

      Org.Lett.

      Volume: 14 Issue: 4 Pages: 1066-1069

    • DOI

      10.1021/ol2031729

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereospecific Cross-Coupling between Alkenylboronates and Alkyl Halides Catalyzed by Iron-Bisphosphine Complexes2012

    • Author(s)
      Hashimoto, T.; Hatakeyama, T.; Nakamura, M.
    • Journal Title

      J.Org.Chem.

      Volume: 77 Issue: 2 Pages: 1163-1173

    • DOI

      10.1021/jo202151f

    • Related Report
      2013 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cross-Coupling of Non-activated Chloroalkanes with Aryl Grignard Reagents in the Presence of Iron/N-Heterocyclic Carbene Catalysts2012

    • Author(s)
      Ghorai, S.K.; Jin, M.; Hatakeyama, T.; Nakamura, M.
    • Journal Title

      Org.Lett.

      Volume: 14 Pages: 1066-1069

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of BN-fused Polycyclic Aromatics via Tandem Intramolecular Electrophilic Arene Borylation2011

    • Author(s)
      Hatakeyama, Takuji; Hashimoto, Sigma; Seki, Shu; Nakamura, Masaharu
    • Journal Title

      Journal of the American Chemical Society

      Volume: 133 Issue: 46 Pages: 18614-18617

    • DOI

      10.1021/ja208950c

    • Related Report
      2013 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Tuning Chemoselectivity in Iron-Catalyzed Sonogashira-type Reaction Using a Bisphosphine Ligand with Peripheral Steric Bulk : Selective Alkynylation of Non-activated Alkyl Halides2011

    • Author(s)
      Hatakeyama, T.; Okada, Y.; Yoshimoto, Y.; Nakamura, M.
    • Journal Title

      Angew.Chem., Int.Ed.

      Volume: 50 Issue: 46 Pages: 10973-10976

    • DOI

      10.1002/anie.201104125

    • Related Report
      2013 Final Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Kumada-Tamao-Corriu Coupling of Alkyl Halides Catalyzed by an Iron-Bisphosphine Complex2011

    • Author(s)
      Hatakeyama, T.; Fujiwara, Y.; Okada, Y.; Itoh, T.; Hashimoto, T.; Kawamura, S.; Ogata, K.; Takaya, H.; Nakamura, M
    • Journal Title

      Chem. Lett

      Volume: 40

    • NAID

      10029522882

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Kumada-Tamao-Corriu Coupling of Alkyl Hal ides Catalyzed by an Iron-Bisphosphine Complex2011

    • Author(s)
      Hatakeyama, T.; Fujiwara, Y.; Okada, Y.; Itoh, T.; Hashimoto, T.; Kawamura, S.; Ogata, K.; Takaya, E.; Nakamura, M.
    • Journal Title

      Chem.Lett.

      Volume: 40 Pages: 1030-1032

    • NAID

      10029522882

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Presentation] ボラナフトペリレン類縁体の合成と物性2014

    • Author(s)
      宮本文也・畠山琢次
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2014-03-30
    • Related Report
      2013 Final Research Report
  • [Presentation] ホウ素を縮環部に有するフェノキサボリン及びフェナザボリン類縁体の合成と物性2014

    • Author(s)
      中嶋貴一・畠山琢次
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2014-03-30
    • Related Report
      2013 Final Research Report
  • [Presentation] ホウ素を縮環部に有するベンゾフェノキサボリン類縁体の合成と物性2014

    • Author(s)
      平井大貴・畠山琢次
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2014-03-30
    • Related Report
      2013 Final Research Report
  • [Presentation] リンを縮環部に有するフェノキサホスフィン類縁体の合成と物性2014

    • Author(s)
      中塚宗一郎・畠山琢次
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Year and Date
      2014-03-30
    • Related Report
      2013 Final Research Report
  • [Presentation] ヘテロール部位を有するホウ素―窒素縮環多環芳香族化合物の合成と物性2013

    • Author(s)
      橋本士雄磨・畠山琢次・中村正治
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学
    • Year and Date
      2013-03-22
    • Related Report
      2013 Final Research Report
  • [Presentation] 電子求引基を有する4b-アザ-12b-ボラジベンゾ[g,p]クリセンの合成と物性2013

    • Author(s)
      青木雄真・橋本士雄磨・畠山琢次・中村正治
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学
    • Year and Date
      2013-03-22
    • Related Report
      2013 Final Research Report
  • [Presentation] BN縮環構造を有する多環芳香族化合物の合成と物性2012

    • Author(s)
      橋本士雄磨・大場剛士・畠山琢次・中村正治
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都テルサ
    • Year and Date
      2012-09-21
    • Related Report
      2013 Final Research Report
  • [Presentation] BN縮環構造を有する螺旋π共役分子の合成と物性2012

    • Author(s)
      畠山琢次・橋本士雄磨・大場剛士・中村正治
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪大学
    • Year and Date
      2012-09-14
    • Related Report
      2013 Final Research Report
  • [Presentation] 求電子的タンデムボリル化反応を活用したホウ素ー窒素縮環芳香族化合物群の合成2012

    • Author(s)
      橋本士雄磨,大場剛士,畠山琢次,関修平,中村正治
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応義塾大学
    • Year and Date
      2012-03-27
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis of BN-fused Polycyclic Aromatics via Tandem Bora-Friedel-Crafts Reaction2011

    • Author(s)
      Hatakeyama, T.; Hashimoto, S.; Nakamura, M
    • Organizer
      The Seventh International Symposium on Integrated Synthesis
    • Place of Presentation
      神戸
    • Year and Date
      2011-10-10
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis of BN-fused Polycyclic Aromatics via Tandem Bora-Friedel-Crafts Reaction2011

    • Author(s)
      Hatakeyama, T; Hashimoto, S.; Nakamura, M.
    • Organizer
      The Seventh International Symposium on Integrated Synthesis (ISIS-7)
    • Place of Presentation
      Kobe, Japan
    • Year and Date
      2011-10-10
    • Related Report
      2011 Annual Research Report
  • [Presentation] Synthesis ofπ-Conjugated Molecules with Heteroatom Junctions via Intramolecular Tandem Hetero Friedel–Crafts Reaction2011

    • Author(s)
      Hashimoto, S.; Hatakeyama, T.; Nakamura, M
    • Organizer
      The 1st Junior International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      上海、中国
    • Year and Date
      2011-07-25
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis of Triarylamines by Iron-Catalyzed Aromatic Amination Reaction2011

    • Author(s)
      Imayoshi, R.Yoshimoto, Y.; Ghorai, S.K.; Hatakeyama, T.; Nakamura, M.
    • Organizer
      16th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS16)
    • Place of Presentation
      Shanghai, China
    • Year and Date
      2011-07-25
    • Related Report
      2011 Annual Research Report
  • [Presentation] Synthesis ofπ-curved molecules with heteroatom junctions via intramolecular tandem hetero-Friedel-Crafts reaction2011

    • Author(s)
      Hashimoto, S.; Oba, T.; Hatakeyama, T.; Nakamura, M
    • Organizer
      5th ChemComm International Symposium
    • Place of Presentation
      京都
    • Year and Date
      2011-05-16
    • Related Report
      2013 Final Research Report
  • [Presentation] Synthesis of π-curved molecules with heteroatom junctions via intramolecular tandem hetero-Friedel-Crafts reaction2011

    • Author(s)
      Hashimoto, S.; Oba, T.; Hatakeyama, T.; Nakamura, M.
    • Organizer
      5th ChemComm International Symposium
    • Place of Presentation
      Kyoto, Japan
    • Year and Date
      2011-05-16
    • Related Report
      2011 Annual Research Report
  • [Presentation] ボラナフトペリレン類縁体の合成と物性

    • Author(s)
      宮本文也・畠山琢次
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] ホウ素を縮環部に有するベンゾフェノキサボリン類縁体の合成と物性

    • Author(s)
      平井大貴・畠山琢次
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] ホウ素を縮環部に有するフェノキサボリン及びフェナザボリン類縁体の合成と物性

    • Author(s)
      中嶋貴一・畠山琢次
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] リンを縮環部に有するフェノキサホスフィン類縁体の合成と物性

    • Author(s)
      中塚宗一郎・畠山琢次
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
  • [Presentation] タンデムボラFriedel-Crafts反応によるアザボラヘリセンの合成

    • Author(s)
      畠山琢次
    • Organizer
      第46回有機金属若手の会
    • Place of Presentation
      宮城蔵王ロイヤルホテル
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] ヘテロナノグラフェンの合成と機能開拓

    • Author(s)
      畠山琢次
    • Organizer
      和歌山県工業技術センター合成技術講演会
    • Place of Presentation
      和歌山県工業技術センター
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] ヘテロール部位を有するホウ素―窒素 縮環多環芳香族化合物の合成と物性

    • Author(s)
      橋本士雄磨・大場剛士・畠山琢次・中村正治
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀,立命館大学
    • Related Report
      2012 Annual Research Report
  • [Presentation] 電子求引基を有する4b-アザ-12b-ボラジベンゾ[g,p]クリセンの合成と物性

    • Author(s)
      青木雄真・橋本士雄磨・畠山琢次・中村正治
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      滋賀,立命館大学
    • Related Report
      2012 Annual Research Report
  • [Presentation] BN縮環構造を有する螺旋π共役分子の合成と物性

    • Author(s)
      畠山琢次・橋本士雄磨・大場剛士・中村正治
    • Organizer
      第59回 有機金属化学討論会
    • Place of Presentation
      大阪,大阪大学
    • Related Report
      2012 Annual Research Report
  • [Presentation] 鉄触媒芳香族アミノ化反応によるアリールアミン類の合成

    • Author(s)
      今吉隆治・吉本祐也・ゴーライ, スジット, K.・畠山琢次・中村正治
    • Organizer
      第59回 有機金属化学討論会
    • Place of Presentation
      大阪,大阪大学
    • Related Report
      2012 Annual Research Report
  • [Presentation] BN縮環構造を有する多環芳香族化合物の合成と物性

    • Author(s)
      橋本士雄磨・大場剛士・畠山琢次・中村正治
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都,京都テルサ
    • Related Report
      2012 Annual Research Report
  • [Book] Organic Reactions, Volume 832014

    • Author(s)
      Nakamura, E.; Hatakeyama, T.; Ito, S.; Ishizuka, K.; Ilies, L.; Nakamura, M.
    • Total Pages
      499
    • Publisher
      Willey
    • Related Report
      2013 Annual Research Report
  • [Remarks] ホームページ等

    • URL

      http://sci-tech.ksc.kwansei.ac.jp/~hatakeyama/index.html

    • Related Report
      2013 Final Research Report
  • [Patent(Industrial Property Rights)] 有機電界発光素子用材料、有 機電界発光素子、表示装置、及び照明装置2014

    • Inventor(s)
      畠山琢次・中塚宗一郎・中嶋貴一・平井大貴・小野洋平・枝連一志・倪静萍・松下武司・生田利昭
    • Industrial Property Rights Holder
      学校法人関西学院・JNC石油化学 株式会社
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2014-028750
    • Filing Date
      2014-02-18
    • Related Report
      2013 Final Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] 有機電界発光素子用材料、有機電界発光素子、表示装置、及び照明装置2014

    • Inventor(s)
      畠山琢次 他8名
    • Industrial Property Rights Holder
      学校法人関西学院大学・JNC石油化学株式会社
    • Industrial Property Rights Type
      特許
    • Filing Date
      2014-02-18
    • Related Report
      2013 Annual Research Report
  • [Patent(Industrial Property Rights)] Material for organic electroluminescent element, organic electroluminescent element, display device, and lighting device2013

    • Inventor(s)
      畠山琢次・中村正治・橋本士雄磨・小野洋平・枝連一志・生田利昭・倪静萍・松下武司
    • Industrial Property Rights Holder
      京都大学・JNC石油化学株式会社
    • Industrial Property Rights Type
      特許
    • Filing Date
      2013-09-11
    • Related Report
      2013 Final Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] Material for organic electroluminescent element, organic electroluminescent element, display device, and lighting device2013

    • Inventor(s)
      畠山琢次 他7名
    • Industrial Property Rights Holder
      京都大学・JNC石油化学株式会社
    • Industrial Property Rights Type
      特許
    • Filing Date
      2013-09-11
    • Related Report
      2013 Annual Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] 多環芳香族化合物2012

    • Inventor(s)
      畠山琢次・中村正治・橋本士雄磨
    • Industrial Property Rights Holder
      京都大学
    • Industrial Property Rights Type
      特許
    • Filing Date
      2012-03-08
    • Related Report
      2013 Final Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] 多環芳香族化合物2012

    • Inventor(s)
      畠山琢次 他7名
    • Industrial Property Rights Holder
      京都大学・JNC石油化学株式会社
    • Industrial Property Rights Type
      特許
    • Filing Date
      2012-09-11
    • Related Report
      2012 Annual Research Report
  • [Patent(Industrial Property Rights)] 多環芳香族化合物2012

    • Inventor(s)
      畠山琢次, 中村正治, 橋本士雄磨
    • Industrial Property Rights Holder
      京都大学
    • Filing Date
      2012-03-09
    • Related Report
      2011 Annual Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] ビスホスフィン化合物、及びビスホスフィン化合物を配位子とする遷移金属触媒、並びにこれらの製造方法2012

    • Inventor(s)
      中村正治, 畠山琢次, 橋本徹, 仲嶋翔, 中川尚久
    • Industrial Property Rights Holder
      京都大学
    • Industrial Property Number
      2012-046272
    • Filing Date
      2012-03-02
    • Related Report
      2011 Annual Research Report

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Published: 2011-04-06   Modified: 2019-07-29  

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