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Creation of Novel Functionalized Redox Systems with Dunamic Electronic Properties

Research Project

Project/Area Number 10440190
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionTokyo Metropolitan University

Principal Investigator

IYODA Masahiko  Tokyo Metropolitan Univ., Professor, 理学研究科, 教授 (50115995)

Co-Investigator(Kenkyū-buntansha) KUWATANI Yoshiyuki  Tokyo Metropolitan Univ., Lecturer, 理学研究科, 助手 (00234625)
YOSHIDA Masato  Tokyo Metropolitan Univ., Lecturer, 理学研究科, 助手 (50137030)
Project Period (FY) 1998 – 2000
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥13,400,000 (Direct Cost: ¥13,400,000)
Fiscal Year 2000: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 1999: ¥3,100,000 (Direct Cost: ¥3,100,000)
Fiscal Year 1998: ¥9,100,000 (Direct Cost: ¥9,100,000)
KeywordsElectric Conductivity / Magnetic Properties / Tetrathiafulvalene / Ferrocene / Radical Salt / π-donor / 電荷移動錯体
Research Abstract

There is considerable current interest in the novel materials with multi-functionalized properties such as electric conductivity, magnetic properties, optical behavior, etc. These multi-functionalized properties have been expected for the π-electron system containing stable radicals and for molecules with d-πinteraction based on inorganic and organic complexes. Thus, we investigated the syntheses and properties of these multi-functionalized molecules.
(1) Tetrathiafulvalene (TTF) Oligomers : Oligomeric TTFs can be expected to show high conductivities and magnetic properties. A radical salt based on this molecule showed a high conductivity and the other revealed a presence of triplet radicals.
(2) Ferrocenyltetrathiafulvalenes (Fc-TTFs) : The GT-complexes and radical salts derived from Fc-TTFs showed interesting electronic properties.
(3) Tetrathiafulvalene with Halogen Substituents : The radical salt of EDO-TTFI_2 with Ni(mnt)_2 revealed, both metallic conductivity and magnetic properties, reflecting a conducting column structure of EDO-TTF and a crystal engineering based on I_2.

Report

(4 results)
  • 2001 Final Research Report Summary
  • 2000 Annual Research Report
  • 1999 Annual Research Report
  • 1998 Annual Research Report
  • Research Products

    (42 results)

All Other

All Publications (42 results)

  • [Publications] Masahiko Iyoda: "Synthesis, Sitructure and Conducting Properties of Halogenated Ethyrene-dioxytetrathafulvalenes"Heterocycles. 54. 833-848 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Masahiko Iyoda: "A Cyclic Oligophenylene Containing Two 1,8-Naphthalene Units Bridged by Two Face-to-Face Biphenyl Linkages Exhibiting Unusual Strain and π-π Interaction"Organic Letters. 2. 2081-2083 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Masahiko Iyoda: "Z-Tribenzo[c, g, k]1,2,5,6-tetradehydro[12]annulene, a Concave π-Electron System"Chemistry Letters. 860-861 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Masahiko Iyoda: "Novel Synthesis or Hexaaryl[3]radialenes via Dibromo[3]dendralene"Tetrahedron Letters. 41. 7059-7064 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Masahiko Iyoda: "Helical Tetrathiafulvalene Oligomers. Synthesis and Properties of Bi-, Ter-, and Quater-tetrathiafulvalenes"Organic Letters. 2. 2217-2220 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Masahiko Iyoda: "Radical-cation Salts Based on Brominaled and Chlorinated Ethylenedioxytetrathiafulvalenes"chemistry letters. 680-681 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] 伊与田正彦: "化学(ナノスケールの分子リング)"化学同人. 2 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M. Iyoda, Y. Kuwatani, E. Ogura, K. Kara, H. Suzuki, T. Takano, K. Takeda, J. Takano, K. Ugawa, M. Yoshida, H. Matsuyama, H. Nishikawa, I. Ikemoto, T. Kato, N. Yoneyama, J. Nishijo, A. Miyazaki, and T. Enok: "Syntheses, Structure and Conducting Properties of Halogenated Ethylenedioxytetrathiafulvalenes"Heterocyles. 54. 833-848 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] T. Yoshida, Y. Kuwatani, K. Hara, M. Yoshida, H. Matsuyama, M. Iyoda, and S. Nagase: "Copper(I), Silver(I), and Gold(I) Complexes of All-Z-Tribenzo[12]annulene"Tetrahedron Lett.. 42. 53-56 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] S. M. H. Kabir, M. Hasegawa, Y. Kuwatani, M. Yoshida, H. Matsuyama, and M. Iyoda: "Synthesis of Biphenylenes and Tetraphenylenes Using Copper-Catalyzed Coupling of Arylzinc intermediates"J. Chem. Soc., Perkin. Trans, I. 159-165 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y. Kuwatani, T. Yoshida, K. Hara, M. Yoshida, H. Matsuyama, and M. Iyoda: "all-Z-Tetrabenzo[16]-and Pentabenzo[20]annulenes, π-Cavitands Binding to Silver Cation"Org. Lett.. 2. 4017-4020 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] S. M. H. Kabir and M. lyoda: "Selectivity of Cyano-Gilman Cuprates : Synthesis of 10-Membered Ring Cyclophanes"J. Chem. Soc., Chem. Commun. 2329-2330 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] S. M. H. Kabir and M. Iyoda: "Selective Synthesis of Tetraphenylenes and Biphenylenes Using Copper-Catalyzed Coupling of Zincacyclopentadienes"Synthesis. 1839-1842 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M. Iyoda, N. Nakamura, M. Todaka, S. Ohtsu, K. Hara, Y. Kuwatani, M. Yoshida, H. Matsuyama, M. Sugita, H. Tachibana, and H. Inoue: "Novel Synthesis of Hexaaryl[3]radialenes via Dibromo[3]-dendralenes"Tetrahedron Lett.. 41. 7059-7064 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] H. Matsuyama, T. Nakamura, and M. Iyoda: "Synthesis of Fischer-Type Alkoxycarbene Complexes Using Diphenylsulfonium Salts Having Functionalized Alkyl Groups"J. Org. Chem.. 65. 4796-4803 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M. Iyoda, K. Fuchigami, A. Kusaka, T. Yoshida, M. Yoshida, H. Matsuyama, and Y. Kuwatani: "Z-Tribenzo[c,g,k]-1,2,5,6-tetradehydro[12]annulene, a Concaveπ-Electron System"Chem. Lett. 860-861 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M. Iyoda, K. Hara, Y. Kuwatani, and S. Nagase: "Helical Tetrathiafulvalene Oligomers. Synthesis and Properties of Bi-, Ter-, and Quarter- tetrathiafulvalenes"Crg. Lett.. 2217-2220 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M. Iyoda, T. Kondo, K. Nakao, K. Hara, Y. Kuwatani, M. Yoshida, and H. Matsuyama: "A Cyclic Oligophenylene Containing Two 1,8-Naphthalene Units Bridged by Two Face-to-Face Biphenyl Linkages Exhibiting Unusual Strain and π-π Interaction"Org. Lett.. 2081-2083 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M. Iyoda, E. Ogura, T. Takano, K. Hara, Y. Kuwatani, T. Kato, N. Yoneyama, J. Nishijo, A. Miyazaki, and Toshiaki Enoki: "Radical-cation Salts Based on Brominated and Chlorinated Ethylenedioxytetrathiafulvalenes"Chem. Lett.. 680-691 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] S. M. H. Kabir, M. Miura, S. Sasaki, G. Harada, Y. Kuwatani, M. Yoshida, and M. Iyoda: "New Syntheses of Tricyclic Thiophenes and CyclicTetrathiophenes Using Transition-Metal-Catalyzed Cyclization"Heterocydes. 52. 761-774 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y. Kuwatani, T. Yoshida, A. Kusaka, and M. Iyoda: "All-Z-Tribenzo[12]-, Tetrabenzo[16]-and Pentabenzo[20]annulenes"Tetrahedron Lett. 41. 359-363 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Masahiko Iyoda et al.: "Synthesis, Structure and Conducting Properties of Haiogenated Ethyrene-dioxytetrathiafulvalenes"Heterocycles. (印刷中).

    • Related Report
      2000 Annual Research Report
  • [Publications] Masahiko Iyoda et al.: "A Cyclic Oligophenylene Containing Two 1, 8-Naphthalene Units Bridged by Two Face-to-Face Biphenyl Linkages Exhibiting Unusual Strain and π-π Interaction."Organic Letters. 2. 2081-2083 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Masahiko Iyoda et al.: "Z-Tribenzo[c,g,k]-1,2,5,6-tetradehydro[12]annulene, a Concave π-Electron System."Chemistry Letters. 860-861 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Masahiko Iyoda et al.: "Novel Synthesis of Hexaaryl[3]radialenes via Dibromo[3]dendralene."Tetrahedron Letters. 41. 7059-7064 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Masahiko Iyoda et al.: "Helical Tetrathiafulvalene Oligomers.Synthesis and Properties of Bi-, Ter-, and Quater-tetrathiafulvalenes."Organic Letters. 2. 2217-2220 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Masahiko Iyoda et al.: "Radical-cation Salts Based on Brominated and Chlorinated Ethylenedioxyletrathiafulvalenes."Chemistry Letters. 680-681 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] 伊与田正彦: "化学(ナノスケールの分子リング)"化学同人. 2 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Masahiko Iyoda: "Conducting charge-transfer and radical ion salts based on bitetrathiafulvalene."J. Mater. Chem.. 9. 335-337 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Masahiko Iyoda: "1,1-Bis(tetrathiafulvalenyl)ethylene. A Unique Cross-Conjugated Dimeric Tetrathiafulvalene."Tetrahedron Lett.. 40. 2807-2810 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Masahiko Iyoda: "Isolation of Two Conformers of Z,Z-Tribenzo [c,g,k]-[12]annulene-1,2-dione."Tetrahedron Lett.. 40. 2961-2964 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Masahiko Iyoda: "Synthesis and Properties of Bitetraselenafulvalene."Tetrahedron Lett.. 40. 5729-5730 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Masahiko Iyoda: "All-Z-Tribenzo[12]-,Tetrabenzo[16]-, Pentabenzo[20]-annulenes."Tetrahedron Lett.. 41. 359-363 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] Masahiko Iyoda: "New Synthesis of Tricyclic Thiophenes and Cyclic Tetrathiophenes Using Transition-Metal-Catalyzed"Heterocycles. 52. 761-774 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] 伊與田正彦: "炭素第三の同素体 フラーレンの化学"学会出版センター. 8 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Masahiko Iyoda: "A One-Step Synthesis of Dehydro[12]annulenes Using Palladium-Catalyzed Reaction of o-Diiodoarenes with Acetylene Gas." Tetrahedron Lett.39. 4701-4704 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Masahiko Iyoda: "Novel Synthesis of Biphenylene and Its Derivatives Using Intramolecular Coupling of Zincacyclopentadienes." Tetrahedron Lett.39. 5393-5396 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Masahiko Iyoda: "Structures and Tropicity of Hydrogenation Products of a Bisdehydro[13]annulenone and Bisdehydro[15]annulenone." Bull.Chem.Soc.Jpn.71. 221-230 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Masahiko Iyoda: "Face-to-Face Fixed Ferrocenes. Synthesis and Properties of 2, 10-Diferrocenyl and 2, 5-, 7, 10-Tetraferrocenyl-1, 6-methano[10]annulene" J.Organomet.Chem.569. 225-233 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Masahiko Iyoda: "Efficient Synthesis of Fullerene Dimers Containing a Fluoroalkyl Group." Tetrahedron Lett.40. 735-736 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Masahiko Iyoda: "Conducting charge-transfer and radical ion salts based on bit bitetrathiafulvalene. An approach to organic metals." J.Mater.Chem.9. 335-337 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Masahiko Iyoda: "“Reactive Organometallics," edited by S.Murahashi, Y.Moro-oka, and A.Yamamoto" Kodansha Ltd., Tokyo, 273-276 (1998)

    • Related Report
      1998 Annual Research Report

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Published: 1998-04-01   Modified: 2016-04-21  

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