• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Synthetic of polyacene/metallocene-fused hybrid pi-conjugated systems

Research Project

Project/Area Number 25620051
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Functional solid state chemistry
Research InstitutionHokkaido University

Principal Investigator

TAKAHASHI Tamotsu  北海道大学, 触媒化学研究センター, 教授 (30163273)

Co-Investigator(Kenkyū-buntansha) OGASAWARA Masamichi  北海道大学, 触媒化学研究センター, 准教授 (70301231)
Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsアセン / メタロセン / 閉環メタセシス / 縮環 / フェロセン / インデニル / フルオレニル / 架橋 / メタセシス / 閉環反応 / ルテニウム
Outline of Final Research Achievements

Synthesis of the hybrid molecules between polyacenes, which are linearly-fused polycyclic benzenoide aromatic compounds, and metallocenes, which are transition-metal-containing aromatic compounds, was examined. As a metallocene scaffold, ferrocene was chosen because of its chemical stability and easier handling, and the construction of acene moieties within the coordination-spheres of ferrocenes was examined.
Introduction of two allylic substituents at the adjacent positions of a single Cp ligand in ferrocene, and treatment of the prepared ferrocene derivative with the Grubbs catalyst facilitated the ring-closing metathesis reaction to give the corresponding dihydroindenyl compound in nearly quantitative yield. Application of a similar reaction to decaallylferrocene gave single-bridged bis(tetrahydrofluorenyl)iron(II) species in high yield via five-fold ring-closing metathesis within a single molecule.

Report

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

    (30 results)

All 2015 2014 2013

All Journal Article (9 results) (of which Peer Reviewed: 9 results,  Acknowledgement Compliant: 1 results) Presentation (21 results) (of which Invited: 2 results)

  • [Journal Article] Simultaneous Induction of Axial and Planar-Chirality in Arene-Chromium Complexes by Molybdenum-Catalyzed Enantioselective Ring-Closing Metathesis2015

    • Author(s)
      K. Kamikawa, S. Arae, W.-Y. Wu, C. Nakamura, T. Takahashi, M. Ogasawara
    • Journal Title

      Chemistry-A European Journal

      Volume: 21 Issue: 13 Pages: 4954-4957

    • DOI

      10.1002/chem.201500226

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Synthesis of Macrocyclic Heterobiaryl Derivatives by Molybdenum-Catalyzed Asymmetric Ring-Closing Metathesis Inducing Winding Vine-Shaped Molecular Asymmetry2015

    • Author(s)
      Y. Okayama, S. Tsuji, Y. Toyomori, T. Mori, S. Arae, W.-Y. Wu, T. Takahashi, M. Ogasawara
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 54 Issue: 16 Pages: 4927-4931

    • DOI

      10.1002/anie.201500459

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantioselective Desymmetrization of 1, 2, 3-Trisubstituted Metallocenes by Molybdenum-Catalyzed Asymmetric Intraannular Ring-Closing Metathesis2015

    • Author(s)
      S. Arae, K. Nakajima, T. Takahashi, M. Ogasawara
    • Journal Title

      Organometallics

      Volume: 34 Issue: 7 Pages: 1197-1202

    • DOI

      10.1021/om5011484

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Coupling of Titanacyclopentadienes with a Cp Ligand and Elimination of One Substituent2014

    • Author(s)
      Mizukami, Y.; Li, H.; Nakajima, K.; Song, Z.; Takahashi, T.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 53 Issue: 34 Pages: 8899-8903

    • DOI

      10.1002/anie.201403226

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Phosphine-Olefin Ligands Based on a Planar-Chiral(π-Arene)chromium Scaffold : Design, Synthesis, and Application in Asymmetric Catalysis2014

    • Author(s)
      M. Ogasawara, Y.-Y. Tseng, S. Arae, T. Morita, T. Nakaya, W.-Y. Wu, T. Takahashi, K. Kamikawa
    • Journal Title

      the Journal of the American Chemical Society

      Volume: 136 Issue: 26 Pages: 9377-9384

    • DOI

      10.1021/ja503060e

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] MnI2-catalyzed dimerization of 2-hydroxyanthracene2013

    • Author(s)
      Zhang, Sicheng; Wang, Yanqing; Song, Zhiyi; Nakajima, Kiyohiko; Takahashi, Tamotsu
    • Journal Title

      Chemistry Letters

      Volume: 42(7) Issue: 7 Pages: 697-699

    • DOI

      10.1246/cl.130251

    • NAID

      10031183263

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Helically Chiral Diene in Asymmetric Catalysis: C2-Symmetric (Z,Z)-2,3-Bis[1-(diphenylphosphinyl)ethylidene]tetralin as Highly Active Lewis-Base Organocatalyst2013

    • Author(s)
      Ogasawara, M.; Kotani, S.; Nakajima, H.; Furusho, H.; Miyasaka, M.; Shimoda, Y.; Wu, W.-Y.; Sugiura, M.; Takahashi, T.; Nakajima, M.
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 52 Issue: 51 Pages: 13798-13802

    • DOI

      10.1002/anie.201308112

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Characterization of Benzo[b]phosphaferrocene Derivatives2013

    • Author(s)
      Ogasawara, Masamichi; Arae, Sachie; Watanabe, Susumu; Subbarayan, Velusamy; Sato, Hiroyasu; Takahashi, Tamotsu
    • Journal Title

      Organometallics

      Volume: 32(17) Issue: 17 Pages: 4997-5000

    • DOI

      10.1021/om400496b

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Aromatic ring construction from zirconocenes and titanocenes2013

    • Author(s)
      Li, Shi; Takahashi, Tamotsu
    • Journal Title

      Transition-Metal-Mediated Aromatic Ring Construction

      Volume: 1 Pages: 299-320

    • DOI

      10.1002/9781118629871.ch11

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] Separation of two carbons and three carbons unit on Titanium2014

    • Author(s)
      Tamotsu Takahashi
    • Organizer
      第16回有機金属化学および配 位化学に関する日韓合同シンポジウム
    • Place of Presentation
      東北大学(宮城県仙台市)
    • Year and Date
      2014-10-24
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Separation of Two Carbons Unit and Three Carbons Unit on Titanium2014

    • Author(s)
      Tamotsu Takahashi
    • Organizer
      7th Negishi-Brown Lectures
    • Place of Presentation
      West Lafayette (USA)
    • Year and Date
      2014-10-06 – 2014-10-07
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Separation of Linearly Aligned 5 Carbons into 2-Carbon Unit and 3-Carbon Unit on Titanium2014

    • Author(s)
      Hsieh, Y.-F.; Song, Z.; Nakajima, K.; Kanno, K.; Takahashi, T.
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学(福岡県福岡市)
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Annual Research Report
  • [Presentation] Application of Carbon-Carbon Bond Cleavage on Titanocene to Indene Derivatives Formation2014

    • Author(s)
      Mizukami, Y.; Li, H.; Nakajima, K.; Song, Z.; Takahashi, T.
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学(福岡県福岡市)
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Annual Research Report
  • [Presentation] Endo-Mode Ring-Closing Metathesis in Cp Manganese Complexes and Their Application to Asymmetric Synthesis2014

    • Author(s)
      Tseng, Y.-Y.; Arae, S.; Wu, Q.; Kamikawa, K.; Takahashi, T.; Ogasawara, M.
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学(福岡県福岡市)
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Annual Research Report
  • [Presentation] Catalytic Asymmetric Synthesis of P-Stereogenic Phosphines by Mo-Catalyzed Asymmetric Ring-Closing Metathesis on (eta6-Arene)chromium Platform2014

    • Author(s)
      Ogasawara, M.; Arae, S.; Tseng, Y.-Y.; Ikehata, R.; Wu, W.-Y.; Takahashi, T.; Kamikawa, K.
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学(福岡県福岡市)
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthesis of Phosphine-Olefin Ligands Based on a Planar-Chiral (Arene)chromium Scaffold and Their Application to Asymmetric Reactions2014

    • Author(s)
      Ogasawara, M.; Tseng, Y.-Y.; Nakaya, T.; Morita, T.; Arae, S.; Wu, W.-Y.; Takahashi, T.; Kamikawa, K.
    • Organizer
      The 26th International Conference on Organometallic Chemistry
    • Place of Presentation
      ロイトン札幌(北海道札幌市)
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] Enantioselective Synthesis of Planar-Chiral Ferrocene-Fused 4-Pyridones and Application in Preparing Library of Pyridine-Based Nucleophilic Organocatalysts2014

    • Author(s)
      Ogasawara, M.; Wada, S.; Isshiki, E.; Yanagisawa, A.; Takahashi, T.; Yoshida, K.
    • Organizer
      The 26th International Conference on Organometallic Chemistry
    • Place of Presentation
      ロイトン札幌(北海道札幌市)
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] Zirconium Catalyzed Carbon-Carbon Bond Formation of Alkynes with EtMgBr2014

    • Author(s)
      Takizawa, S.; Hsieh, Y.-F.; Song, Z.; Takahashi, T.
    • Organizer
      The 26th International Conference on Organometallic Chemistry
    • Place of Presentation
      ロイトン札幌(北海道札幌市)
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthesis of Acene Dimers Catalyzed by Manganese2014

    • Author(s)
      Zhang, S.; Song, Z.; Nakajima, K.; Takahashi, T.
    • Organizer
      The 26th International Conference on Organometallic Chemistry
    • Place of Presentation
      ロイトン札幌(北海道札幌市)
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] Synthesis and Applications of Ferrocene-Fused Planar-Chiral Phospholes2014

    • Author(s)
      Ogasawara, M.; Hu, H.; Wu, W.-Y.; Nakajima, K.; Takahashi, T.
    • Organizer
      The 26th International Conference on Organometallic Chemistry
    • Place of Presentation
      ロイトン札幌(北海道札幌市)
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] Separation of Linearly Aligned 5-Carbons into 2-Carbon Units and 3-Carbon Units on Titanium2014

    • Author(s)
      Hsieh, Y.-F.; Song, Z.; Nakajima, K.; Kanno, K.; Takahashi, T.
    • Organizer
      The 26th International Conference on Organometallic Chemistry
    • Place of Presentation
      ロイトン札幌(北海道札幌市)
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] Titanium Mediated Double Carbon-Carbon Bond Cleavage Reaction2014

    • Author(s)
      Mizukami, Y.; Song, Z.; Nakajima, K.; Takahashi, T.
    • Organizer
      The 26th International Conference on Organometallic Chemistry
    • Place of Presentation
      ロイトン札幌(北海道札幌市)
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] Catalytic Preparation of Planar-Chiral Functional Metallocenes by Asymmetric Ring-Closing Metathesis and Their Applications2014

    • Author(s)
      Ogasawara, M.; Arae, S.; Watanabe, S.; Oana, A.; Nakajima, K.; Takahashi, T.
    • Organizer
      The 26th International Conference on Organometallic Chemistry
    • Place of Presentation
      ロイトン札幌(北海道札幌市)
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] “Selective Synthesis of Second Ring Adducts of Pentacene and Their Thermal Decomposition”2014

    • Author(s)
      Yi-Fang Hsieh, Zhiying Jia, Kiyohiko Nakajima, Zhiyi Song, Tamotsu Takahashi
    • Organizer
      統合物質国際シンポジウム in 福岡
    • Place of Presentation
      九州大学(福岡市)
    • Related Report
      2013 Research-status Report
  • [Presentation] マンガン触媒による2-ヒドロキシアントラセンの二重化反応2013

    • Author(s)
      張 四成・宋 志毅・中島 清彦・高橋 保
    • Organizer
      第25回万有札幌シンポジウム
    • Place of Presentation
      北海道大学工学部オープンホール(札幌市)
    • Related Report
      2013 Research-status Report
  • [Presentation] メタル化ペンタセンの合成2013

    • Author(s)
      王延卿・宋志毅・中島清彦・高橋保
    • Organizer
      日本化学会北海道支部2013年夏季研究発表会
    • Place of Presentation
      北見工業大学(北見市)
    • Related Report
      2013 Research-status Report
  • [Presentation] 多環芳香族の二量化反応2013

    • Author(s)
      張四成・宋志毅・中島清彦・高橋保
    • Organizer
      日本化学会北海道支部2013年夏季研究発表会
    • Place of Presentation
      北見工業大学(北見市)
    • Related Report
      2013 Research-status Report
  • [Presentation] ペンタセン2nd リング付加体の合成2013

    • Author(s)
      謝宜芳・賈志英・宋志毅・中島清彦・
    • Organizer
      日本化学会北海道支部2013年夏季研究発表会
    • Place of Presentation
      北見工業大学(北見市)
    • Related Report
      2013 Research-status Report
  • [Presentation] “Synthesis of Transition Metal Substituted Pentacene Derivatives”2013

    • Author(s)
      Yanqing Wang, Zhiying Jia, Zhiyi Song, Kiyohiko Nakajima, Tamotsu Takahashi
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2013 (C&FC 2013)
    • Place of Presentation
      Renmin University of China(China)
    • Related Report
      2013 Research-status Report
  • [Presentation] “Synthesis of Palladium Substituted Pentacene Derivatives”2013

    • Author(s)
      王 延卿、宋 志毅、高橋 保
    • Organizer
      第4回統合物質シンポジウム
    • Place of Presentation
      北海道大学創成科学研究棟(札幌市)
    • Related Report
      2013 Research-status Report

URL: 

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

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi