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Creation of New pi-Electron Systems with Novel Properties and Functions

Research Project

Project/Area Number 04453027
Research Category

Grant-in-Aid for General Scientific Research (B)

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionTokyo Metropolitan University

Principal Investigator

IYODA Masahiko  Faculty of Science, Tokyo Metropolitan University, Professor, 理学部, 教授 (50115995)

Co-Investigator(Kenkyū-buntansha) SASAKI Shigeru  Faculty of Science, Tokyo Metropolitan University, Research Assistant, 理学部, 助手 (90254143)
YOSHIDA Masato  Faculty of Science, Tokyo Metropolitan University, Research Assistant, 理学部, 助手 (50137030)
MATSUYAMA Haruo  Faculty of Science, Tokyo Metropolitan University, Assistant Professor, 理学部, 助教授 (30087118)
Project Period (FY) 1992 – 1993
Project Status Completed (Fiscal Year 1993)
Budget Amount *help
¥7,100,000 (Direct Cost: ¥7,100,000)
Fiscal Year 1993: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 1992: ¥5,700,000 (Direct Cost: ¥5,700,000)
Keywordsconductivity / Ferromagnetic interaction / donor / tetrathiafulvalene / ferrocene / palladium catalyzed reaction / cross-coupling / radical salt / 半導体 / [3]ラジアレン / アフセプター / ジアニオン / CT錯体
Research Abstract

In order to create the compounds which have both conductivity and ferromagnetic properties, we designed the donor systems bearing TTF- or ferrocene-unit at the 1,3-or 1,3,5-positions of aromatic rings. The donor molecules with TTF-units have been synthesized using the palladium-catalyzed cross-coupling reaction of tetrathiafulvalenyltin with halogenated benzene derivatives. The dication diradicals and trication triradicals prepared from the TTF-donors show conductivity like a semi-conductor. However, these radical salts indicate almost no ferromagnetic interaction between radical centers. The donor molecules with ferrocene-units have been synthesized by the palladium-catalyzed cross-coupling reaction of ferrocenylzinc reagent with halogenated benzene derivatives. This reaction easily produces the products in a one-pot procedure. The dication diradical or trication triradical salts of the ferrocenedonor show some interaction of ferrocenyl irons. However, the conductivity measurements of this system indicate that the radical salts are a insulator.

Report

(3 results)
  • 1993 Annual Research Report   Final Research Report Summary
  • 1992 Annual Research Report
  • Research Products

    (25 results)

All Other

All Publications (25 results)

  • [Publications] Masahiko Iyoda: "Synthesis of the Tris(9-fluorenylidene)cyclopropane Dianion and Related Dianions:3 Radialenes with Novel Electronic Properties" Angew.Chem.,Int.Ed.Engl.32. 89-90 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Masato Yoshida: "Convenient Preparation and Michael Reactions of 4-Fluoroalkylated But-2-en-4-olides" J.Chem.Soc.,Perkin Trans.1. 501-504 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Masato Yoshida: "Reaction of C_<60> with Diacyl Peroxides Containing Perfluoroalkyl Groups.The First Example of Electron Transfer Reaction via C_<60>^+" Tetrahedron Letters. 34. 7629-7632 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Hideki Saitoh: "Crystal Structures of the Room-Temperature Phase of 4,4''-Difluoro-p-terphenyl and 4,4'''-Difluoro-p-quaterphenyl" Bull.Chem.Soc.Jpn.66. 2847-2853 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Masahiko Iyoda: "Synthesis of (1,5-Diazabicyclo 4.3.0 nonan-2-ylidene-pentacarbonylchromium and -tungsten Using Reaction of Carbene Complexes with 6-Membered Hydrazine" Chem.Lett.777-778 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Masahiko Iyoda: "Synthesis and Properties of Platinum Complexes of Fullerenes(C_<60> and C_<70>)" Fullerene Science and Technology. (in press). (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Masahiko Iyoda, Hiroyuki Kurata, Masaji Oda, Chiaki Okubo, and Kichisuke Nishimoto: ""Synthesis of the Tris(9-fluorenylidene)cyclopropane. Dianion and Related Dianions : [3]Radialenes with Novel Electronic Properties"" Angew.Chem., Int.Ed.Engl.32. 89-90 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Hiroyuki Higuchi, Masao Kondo, Hiroko Yonehara, Juro Ojima, and Masahiko Iyoda: ""Synthesis of 1-(2,2-Dicyanovinyl)-, 1-(2,4,4-Tricyano-1,3-butadienyl)-, 1,6-Bis(2,2-dicyanovinyl)-1,3,5-cycloheptatriene and Their Vinylogs"" Bull.Chem.Soc.Jpn.66. 275-281 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Hiroyuki Higuchi, Hiroyuki Yamamoto, Masahiko Iyoda, Masato Yoshida, and Gaku Yamamoto: ""Synthesis of Methano-bridged Tetradehydro[36]annulene"" J.Chem.Soc., Perkin Trans.1. 983-986 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Masato Yoshida, Rihoko Imai, Yoji Komatsu, Yoshihiro Morinaga, Norimasa Kamigata, and Masahiko Iyoda: ""Convenient Preparation and Michael Reactions of 4-Fluoroalkylated But-2-en-4-olides"" J.Chem.Soc., Perkin Trans.1. 501 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Masato Yoshida, Yoshihiro Morinaga, Masahiko Iyoda, Koichi Kikuchi, Isao Ikemoto, and Yohji Achiba: ""Reaction of C_<60> with Diacyl Peroxides Containing Perfluoroalkyl Groups. The First Example of Electron Transfer Reaction via C60^+ in solution"" Tetrahedron Lett.34. 7629-7632 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Hideki Saitoh, Kazuya Saito, Yasuhisa Yamamura, Haruo Matsuyama, Koichi Kikuchi, Masahiko Iyoda, and Isao Ikemoto: ""Crystal Structures of the Room-Temperature Phase of 4,4" -Difluoro-p-terphenyl and 4,4" - Difluoro-p-quaterphenyl"" Bull.Chem.Soc.Jpn.66. 2847-2853 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Masahiko Iyoda, Li Zhao, and Haruo Matsuyama: ""Synthesis of (1,5-Diazabicyclo[4.3.0]nonan-2-ylidene)pentacarbonylchromium and -tungsten Using Reaction of 2-Unsaturated Carbene Complexes with 6-Membered Hydrazine"" Chem.Lett.777 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Masahiko Iyoda, Yoshio Ogawa, Haruo Matsuyama, Hisanori Ueno, Koichi Kikuchi, Isao Ikemoto, and Yohji Achiba: ""Synthesis and Properties of Platinum Complexes of Fullerenes (C_<60> and C_<70>)"" Fullerene Science and Technology. in press.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Masahiko Iyoda: "Synthesis of the Tris(9-fluorenylidene)cyclopropane Dianion and Related Dianions:〔3〕Radialenes with Novel Electronic Properties" Angew.Chem.,Int.Ed.Engl.32. 89-90 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Masato Yoshida: "Convenient Preparations and Michael Reactions of 4-Fluoroalkylated But-2-en-4-olieds." J.Chem.Soc.,Perkin Trans.1,. 501-504 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Masato Yoshida: "Reaction of C_<60> with Diacyl Peroxides Containing Perfluoroalky.Groups.The First Example of Electron Transfer Reaction via C_<60>" Tetrahedron Letters. 34. 7629-7632 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Hideki Saitoh: "Crystal Structures of the Room-Temperature Phase of 4,4″-Difluoro-p-terphenyl and 4,4′″-Difluror-p-quaterphenyl" Bull.Chem.Sco.Jpn.

    • Related Report
      1993 Annual Research Report
  • [Publications] Masahiko Iyoda: "Synthesis of (1,5-Diazabicyclo〔4.3.0〕nonan-2-ylidene)penta-carbonylchromium and-tungsten Using Reaction of Carbene Complex" Chemistry Letters. (in press). (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Masahiko Iyoda: "Synthesis and Properties of Platinum Complexes of Fullerenes(C_<60> and C_<70>)" Fullerene Science and Technology. (in press).

    • Related Report
      1993 Annual Research Report
  • [Publications] Masahiko Iyoda: "Palladium-catalyzed Coupling of Trialkylstannyltetrathiafulvalenes with Aryl Halides" J.Chem.Soc.,Chem.Commun.158-159 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Masahiko Iyoda: "A Novel C=C Bond Cleavage in Hexacarbonyl(hexapentaene)diiron:X-Ray Crystal Structure of a Bis(μ_3,μ^2-allenylidene)-Iron Complex" J.Chem.Soc.,Chem.Commun.399-400 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Takako Nakamura: "Synthesis of Macrocyclic Dilactones by Cyclization of Sulfonium Salts" J.Org.Chem.57. 3783-3789 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Hiroyuki Higuchi: "Synthesis of 1-(2,2-Dicuamoyimyl)-,1-(2,4,4-Tricyano-1,3-butadienyl)-,1,6-Bis(2,2-dicyanovinyl)-1,3,5-cycloheptatriene and Their Vinylogs" Bull.Chem.Soc.Jpn.66. 275-281 (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] Masahiko Iyoda: "Synthesis of the Tris(9-fluorenylidene)cyclopropane Dianion and Related Dianions:[3]Radialenes with Novel Electronic Properties" Angew.Chem.,Int.Ed.Engl.32. 89-90 (1993)

    • Related Report
      1992 Annual Research Report

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Published: 1992-04-01   Modified: 2016-04-21  

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