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Design and Synthesis of Novel Elctron-Conductive Materials and Usage as Functionalized Materials for Information

Research Project

Project/Area Number 05403025
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field 有機工業化学
Research InstitutionOkayama University

Principal Investigator

TORII Sigru  Okayama Univ., Dept.of Applied Chemistry, Professor, 工学部, 教授 (70032927)

Co-Investigator(Kenkyū-buntansha) GENBA Akiko  Okayama Univ., Dept.of Applied Chemistry, Research Associate, 工学部, 教務員 (80274009)
OKUMOTO Hiroshi  Kurashiki Univ.of Science and Arts, Dept.of Chemical Technology, Associate Profe, 産業科学技術学部, 助教授 (90183251)
INOKUCHI Tsutomu  Okayama Univ., Dept.of Applied Chemistry, Associate Professor, 工学部, 助教授 (50168473)
KUROBOSHI Manabu  Okayama Univ., Dept.of Applied Chemistry, Lecturer, 工学部, 講師 (30242316)
TANAKA Hideo  Okayama Univ., Dept.of Applied Chemistry, Associate Professor, 工学部, 助教授 (60032950)
Project Period (FY) 1993 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥31,800,000 (Direct Cost: ¥31,800,000)
Fiscal Year 1996: ¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 1995: ¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 1994: ¥6,800,000 (Direct Cost: ¥6,800,000)
Fiscal Year 1993: ¥19,200,000 (Direct Cost: ¥19,200,000)
KeywordsN-oxyl radical / Electron conduction / Polyaniline / Thiophene / Conductive Polymer / Redox / Rechargeable battery / Electro-polymerization / N-オキシルラジカル / チオフェン / 高機能性材料
Research Abstract

Recently, new materials possessing unique elctronic and magnetic properties have been desired, and it is strongly required to establish the guide to design these materials. In this project, some new materials, especially bearing redox funcitnalities such as triarylamine (Ar_3N) and N-oyxl moieties, were synthesized, and their redox properties and spi-spin interactions were estimated.
Anilines substituted by Ar_3N and TEMPO were electro-polymerized to afford electro-conductive polyaniline films on the electrode. These functinalized electrodes are expected to be an electrode in rechargeable batteries.
Redox properties of some TEMPO derivatives were studied under various electrolysis conditions. These compounds are found to be interconverted between N-hydroxyl, N-oxyl and N-oxoammonium, reversibly, and work as effective oxidants of alcohols.
Regulation of spins of stable radical materials is very important to realize organoferromagnetics. We have developed a convenient method to synthesize poly-N-oxyl compounds in which N-oxyl moieties were connected by p-electron systems. Spin-spin interactions were detected by ESR spectroscopy.

Report

(5 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report
  • 1994 Annual Research Report
  • 1993 Annual Research Report
  • Research Products

    (43 results)

All Other

All Publications (43 results)

  • [Publications] Sigeru TORII: "Palladium-Catalyzed Sequential Bond Formation Leading to Conjugated Ene-Yne System" Tetrahedron Lett.34. 2139-2142 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 井口勉: "ニトロキシル化合物を用いるアルコールの触媒的酸化反応の進歩" 有機合成化学協会誌. 51. 910-920 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 鳥居滋: "有機電解合成における有機金属錯体" 有機合成化学協会誌. 51. 1024-1042 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Tsutomu INOKUCHI: "Electrochemical Wacker Type Reactin with a double Mediatory System Consisting of Palladium Complex and Tri (4-bromophenyl) amine" Chem.Lett.121-124 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Tsutomu INOKUCHI: "Oxidations of Dihydroxyalkanoates to Vicinal Tricarbonyl Compounds with a 4-Bzo TEMPO-Sodium Bromite System or by Indirect Electrolysis with 4-Bzo TEMPO and Bromide Ion" Chem.Lett.1411-1414 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Sigeru TORII: "Electrochemical Os-Catalyzed Asymmetric Dihydroxylation of Olefins with Sharpless'Ligand" Chem.Lett.319-320 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Sigeru TORII: "Electrochemical Deamination of Aromatic Amines" Synlett. 439-440 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Sigeru TORII: "A Novel Ru(VII)/Ru(IV)Mediatory System for Electrooxidation of Primary and Secondary Alcohols,Leading to Aldehydes and Ketones" Chem. Lett.369-370 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Tsutomu INOKUCHI: "One-pot Conversion of Primary Alcohols to a-Oxygenated Alkanals with TEMPO in Combination with Molecular Oxygen and Ruthenium Complex" Tetrahedron Lett.36. 3223-3226 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Hideo TANAKA: "Electrooxidative Fission of Carbon-Carbon Double Bond in a K_2OsO_2(OH)_4/HIO_4Double Mediatory System" Bull.Chem.Soc.Jpn.68. 2989-2992 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Sigeru TORII: "Chemical and Electrochemical Asymmetric Dihydroxylation of Olefines in I_2-K_2CO_3-K_2OsO_2O(OH)_4and I_2-K_3PO_4/K_3HPO_4-K_2OsO_2(OH)_4Systems with Sharpless'Ligand" J.Org.Chem.61. 3055-3060 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Hideo TANAKA: "Electropolymerization of Anilines Linked with Triarylamines as a Redox-Active Function" Electrochim.Acta.,. (印刷中). (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Sigeru TORII: "Palladium-Catalyzed Sequential Bond Formation Leading to Conjugated Ene-Yne System" Tetrahedron Lett.34. 2139-2142 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Tsutomu INOKUCHI: "Recent Advances in the Catalytic Oxidation of alcohols with 2,2,6,6-Tetramethylpiperidine-1-oxyl (TEMPO) and Its Application to Organic Synthesis" J.Synth.Org.Chem., Jpn.51. 910-920 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Sigeru TORII: "Organometal Complexes in Electroorganic Synthesis" J.Synth.Org.Chem., Jpn.51. 1024-1042 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Tsutomu INOKUCHI: "Electrochemical Wacker Type Reaction with a double Mediatory System Consisting of Palladium Complex and Tri (4-bromophenyl) amine" Chem.Lett.121-124 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Tsutomu INOKUCHI: "Oxidations of Dihydroxyalkanoates to Vicinal Tricarbonyl Compounds with a 4-Bzo TEMPO-Sodium Bromite System or by Indirect Electrolysis with 4-Bzo TEMPO and Bromide Ion" Chem.Lett.1411-1414 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Sigeru TORII: "Electrochemical Os-Catalyzed Asymmetric Dihydroxylation of Olefins with Sharpless' Ligand" Chem.Lett.319-320 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Sigeru TORII: "Electrochemical Deamination of Aromatic Amines" Synlett.439-440 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Sigeru TORII: "A Novel Ru (VII) /Ru (IV) Mediatory System for Electrooxidation of Primary and Secondary Alcohols, Leading to Aldehydes and Ketones" Chem.Lett.369-370 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Tsutomu INOKUCHI: "One-pot Conversion of Primary Alcohols to alpha-Oxygenated Alkanals with TEMPO in Combination with Molecular Oxygen and Ruthenium Complex" Tetrahedron Lett.36. 3223-3226 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Hideo TANAKA: "Electooxidative Fission of Carbon-Carbon Double Bond in a K_2OsO_2 (OH) _4/HIO_4Double Mediatory System" Bull.Chem.Soc.Jpn.68. 2989-2992 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Sigeru TORII: "Chemical and Electrochemical Asymmetric Dihydroxylation of Olefines in I_2-K_2CO_3-K_2OsO_2 (OH) _4 and I_2-K_3PO_4/K_3HPO_4-K_2OsO_2 (OH) _4 Systems with Sharpless' Ligand" J.Org.Chem.61. 3055-3060 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Hideo TANAKA: "Electropolymerization of Anilins Linked with Triarylamines as a Redox-Active Function" Electrochim.Acta.(in Press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.TANAKA: "Electroreductive Cleavage of Propargylic Acetates throygh Polarity Inversion of in situ Generated Allenyl Palladium (II) Complexes and,in Part,Unisual Chemical Reduction Induced by Phosphine Ligand" ELECTRONALYSIS. 8. 769-772 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] S.TORII: "Chemical and Electrochemical Asymmetric Dihydroxylation of Olefins in I_2-K_2CO」- K_2OsO_2(OH)_4 and I_2-K_3PO_4/K_2HPO_4-K_2OsO_2(OH)_4 Systems with Sharpless' Ligan" J.ORG.CHEM.61. 3055-3060 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] S.TORII: "A Versatle Cycloaddition for the Generation of Pyrrolidine Derivatives via C-N-C 1,3-Dipoles" CHEM.LETT.747-748 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] C.AMATORE: "Oxidative Addition of Aryl Halides to Transient Anionic σ-Aryl-Palladium(o) Intermediates -Application to Palladium-catalyzed Reductive Coupling of Aryl Halides" CHEM.EUR.J.2. 957-965 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] S.Torii: "Electrochemical Os-Catalyzed Asymmetric Dihydroxylation of Olefins with Sharpless′Ligand" Chem.Lett.319-320 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] S.Torii: "Electrochemical Deamination of Aromatic Amines" Synlett. 439-440 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] S.Torii: "A Novel Ru (VII) /Ru (IV) Mediatory System for Electrooxidation of Primary and Secondary Alcohols,Leading to Aldehydes and Ketones" Chem.Lett.369-370 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] S.Torii: "Synthesis of dl-Shikonin by Vanadium (II) -Assisted Cross-Coupling and Electrooxidation of Aromatic Nucleus" Bull.Chem.Soc.,JPN.68. 2917-2922 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] T.Inokuchi: "One-pot Conversion of Primary Alcohols to α-Oxygenated Alkanals with TEMPO in Combination with Molecular Oxygen and Ruthenium Complex" Tetrahedron Lett.36. 3223-3226 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] H.Tanaka: "Use of Aluminium as an Electron Pool.Reductive Coupling of Iodobenzens Promoted by Electron Transfer in an Ni/Pb/Al Multi Redox System" Inoraganica Chimica Acta. 222. 323-325 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] H.Tanaka: "A Facile Access to 3-Allyl-and 3-Benzyl-3-cephems via Reductive Addition/Cyclization of Allenecarboxylate with Allyl and Benzyl Helides in an Al/Pb/Ni Redox System" J.Chem.Soc.Chemical Communications. 1461-1462 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] T.Inokuchi: "Oxidations of Dihydroxyalkanoates to Vicinal Tricarbonyl Compounds with a 4-Bzo TEMPO-Sodium Bromite System or by Indirect Electrolysis with 4-Bzo TEMPO and Bromide Ion" Chemistry Letter. 1411-1414 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] T.Inokuchi: "Baeyer-Villiger Type Oxidation in a Dioxygen-Arenecarbal dehyde-Ruthenium Dioxide or Manganese Dioxide System" Synlett. 12. 1037-1038 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] H.Tanaka: "Palladium-Catalyzed Carbonylative[2+2]Cycloaddition for the Stereoselective Sysnthesis of Either cis-or trans-3-Alkenyl-β-Lactams" J.Org.Chem.59. 3040-3046 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] S.Torii: "Electrochemical Generation of C-N-C 1,3-Dipole Leading to Pyrrolidine Skeleton" Synlett. 3. 217-218 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] T.Inokuchi: "Electrochemical Wacker Type Reaction with a double Mediatory System Consisting of Palladium Complex and Tri(4-bromophenyl)amine" Chemistry Letter. 121-124 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] T.Inokuchi: "Indirect Electrochemical Radical Cyclization of Bromo Acetals by the Combined Use of Cobaloxime and Sacrificial Electrode" Bull.Chem.Soc.Jpn.(1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] S.Torii: "Carbonylative[2+2]Cycloaddition for the Construction of β-Lactam Skeleton with Palladium Catalyst" TETRAHEDRON LETT.34. 6553-6556 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] H.Tanaka: "2-Substituted Penems,New Candidates for Cephalosporinase Inhibitors" Bioorganic & Medicinal Chemistry Letters. 2253-2254 (1993)

    • Related Report
      1993 Annual Research Report

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Published: 1993-04-01   Modified: 2016-04-21  

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