Synthesis of Heterographenes via Tandem Hetero-Friedel-Crafts Reactions

2013 Fiscal Year Final Research Report

• Project/Area Number: 23685020
• Research Category: Grant-in-Aid for Young Scientists (A)
• Allocation Type: Single-year Grants
• Research Field: Synthetic chemistry
• Research Institution: Kwansei 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
• 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.

Research Products

• [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 Reactivity (2013)
  • 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
  • DOI: 10.1002/chem201203189
  • Peer Reviewed
• [Journal Article] Iron-Catalyzed Aromatic Amination for Nonsymmetrical Triarylamine Synthesis (2012)
  • Author(s): Hatakeyama, T.; Imayoshi, R.; Yoshimoto, Y.; Ghorai, S. K.; Jin, M.; Takaya, H.; Norisue, K.; Sohrin, Y.; Nakamura, M Nakamura, M
  • Journal Title: J. Am. Chem. Soc Volume: 134 Pages: 20262–20265
  • DOI: 10.1021/ja309845k
  • Peer Reviewed
• [Journal Article] Azaboradibenzo[6]helicene : Carrier Inversion Induced by Helical Homochirality (2012)
  • Author(s): Hatakeyama, T.; Hashimoto, S.; Oba, T.; Nakamura, M
  • Journal Title: J. Am. Chem. Soc Volume: 134 Pages: 19600–19603
  • DOI: 10.1021/ja310372f
  • Peer Reviewed
• [Journal Article] Iron-Catalyzed Alkyl-Alkyl Suzuki -Miyaura Coupling (2012)
  • 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 Pages: 8834–8837
  • DOI: 10.1021/ja103973a
  • Peer Reviewed
• [Journal Article] Cross-Coupling of Non-activated Chloroalkanes with Aryl Grignard Reagents in the Presence of Iron/N-Heterocyclic Carbene Catalysts (2012)
  • Author(s): Ghorai, S. K.; Jin, M; Hatakeyama, T.; Nakamura, M
  • Journal Title: Org. Lett Volume: 14 Pages: 1066–1069
  • DOI: 10.1021/ol2031729
  • Peer Reviewed
• [Journal Article] Stereospecific Cross-Coupling between Alkenylboronates and Alkyl Halides Catalyzed by Iron-Bisphosphine Complexes (2012)
  • Author(s): Hashimoto, T.; Hatakeyama, T.; Nakamura, M
  • Journal Title: J. Org. Chem. Volume: 77 Pages: 1163–1173
  • DOI: 10.1021/jo202151f
  • Peer Reviewed
• [Journal Article] Synthesis of BN-fused Polycyclic Aromatics via Tandem Intramolecular Electrophilic Arene Borylation (2011)
  • Author(s): Hatakeyama, T.; Hashimoto, S.; Seki, S.; Nakamura, M
  • Journal Title: J. Am. Chem. Soc Volume: 133 Pages: 18614–18617
  • DOI: 10.1021/ja208950c
  • 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 Halides (2011)
  • Author(s): Hatakeyama, T.; Okada, Y.; Yoshimoto, Y.; Nakamura, M
  • Journal Title: Angew. Chem. Int. Ed Volume: 50 Pages: 10973–10976
  • DOI: 10.1002/anie.201104125
  • Peer Reviewed
• [Journal Article] Kumada-Tamao-Corriu Coupling of Alkyl Halides Catalyzed by an Iron-Bisphosphine Complex (2011)
  • 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 Pages: 1030–1032
  • DOI: 10.1246/cl2011.1030
  • 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
• [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
• [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
• [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
• [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
• [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
• [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
• [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
• [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
• [Presentation] Synthesis of BN-fused Polycyclic Aromatics via Tandem Bora-Friedel-Crafts Reaction (2011)
  • 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
• [Presentation] Synthesis ofπ-Conjugated Molecules with Heteroatom Junctions via Intramolecular Tandem Hetero Friedel–Crafts Reaction (2011)
  • 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
• [Presentation] Synthesis ofπ-curved molecules with heteroatom junctions via intramolecular tandem hetero-Friedel-Crafts reaction (2011)
  • 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
• [Remarks] ホームページ等
  • URL: http://sci-tech.ksc.kwansei.ac.jp/~hatakeyama/index.html
• [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: 特願2014-28750
  • Filing Date: 2014-02-18
  • Overseas
• [Patent(Industrial Property Rights)] Material for organic electroluminescent element, organic electroluminescent element, display device, and lighting device (2013)
  • 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
  • Industrial Property Number: WO2014/042197
  • Filing Date: 2013-09-11
  • 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
  • Industrial Property Number: WO2010/104047
  • Filing Date: 2012-03-08
  • Overseas