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SYNTHESES OF NEW ORGANIC ELECTRON DONORS,ACCEPTORS,AND THEIR CHARGE-TRANSFER COMPLEXES,AND STUDIES ON THEIR PROPERTIES

Research Project

Project/Area Number 09640700
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 機能・物性・材料
Research InstitutionKINKI UNIVERSITY

Principal Investigator

OGURA Fumio  KINKI UNIVERSITY,DEPARTMENT OF INDUSTRIAL CHEMISTRY,PROFESSOR, 工学部, 教授 (90028150)

Co-Investigator(Kenkyū-buntansha) OKADA Yoshiharu  KINKI UNIVERSITY,DEPARTMENT OF INDUSTRIAL CHEMISTRY,LECTURER, 工学部, 講師 (30253553)
Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥3,100,000 (Direct Cost: ¥3,100,000)
Fiscal Year 1998: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1997: ¥2,400,000 (Direct Cost: ¥2,400,000)
KeywordsOrganic Electric Conductors / Charge-Transfer Complexes / Organic electron Donors / Organic Electron Acceptors / Pleiadiene Derivatives / Tellurophene-TCNO / Phenanthrene-TCNQ / Chrysene-TCNQ / 新規有機電子供与体 / 新規有機電子受容体 / ヘテロ-TCNQ / 16族ヘテロ原子化合物 / 芳香族π-電子系化合物 / 有機電荷移動錯体
Research Abstract

The target molecules of this research projects are novel organic electron donors (1) and acceptors (2, 3, 4), which are expected to act as effective components to form charge-transfer complexes exhibiting high electric conductivities. The molecule, 1, carries two 7pi electron rings fused to a naplithalenene at its two peri-positions and is expected to behave as a good electron donor in the two stage redox processes. Synthesis of 1 is started from acenaphthene and are first dichiorinated its peri-positins then transformed its 5-membered ring to a cyclic anhydride via bromination with NBS and the following oxidation. The diol obtained by LAH reduction of the anhydride was transformed to 1, 8-Bis(dibromomethyl)4, 5-dichioronaphthalene. The dibromide was reacted with cis-4, 5-bis(boryl)octene, prepared from bis[pinacolato]diboron and 4-octyne, to yield a pleiadene. Efforts to obtain 1 (R=n-Pr) in progress. Tellurophene-TCNQs (2) are only ones left unknown amoung Hetero-TCNQs. Synthesis of … More 2 is started from tellurophene, which is prepared by 1,4-bis(TMS)-1, 3-butadiyne and Na_2Te and then converted to 2, 5-dicarboxylic acid via 6 steps. Transformation of carboxyl group to dicyanomethylene group to obtain 2 (xl, R=H) is now actively sudying. Crysene-TCNQ (3) has a unique extended conjugated pi-system and expected to be very stable and have very low coulombic repulsion in their oxidation states. Their synthesis are planned to couple a 2-bromo-6-methoxynaphthalene and 2-bromo-5-methoxybenzaldehyde by Suzuki-Miyaura method to yield a key intermediate to lead 2, 8-dimethoxyclirysene. The coupling reaction is now scrutinized. Phenanthrene-TCNQ (4) is unique and assumed to be a strong acceptor, because it has a oquinoid partial structure. Its synthesis is planned to execute via a biphenyl derivative, which is obtained from 2-bromo-5-methoxytoluene and N,N-diethy1-4-methoxybenzamide by a combination of Suzuki-Miyaura and Snieckus coupling methods. The biphenyl derivative is subjected to metalatation, intramnoleculari condensation followed dehydroxylic elimination to afford a key phenanthrene derivative, 3, 6-dimethoxyphenanthrene. Now we are actively investigating coupling reaction conditions and procedures to obtain the biphenyl derivatives. Although we do not yet have the target molecules in our hands, we are closely approaching our targets and very sure to be able to get them in near future. Less

Report

(3 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • Research Products

    (29 results)

All Other

All Publications (29 results)

  • [Publications] Nakata Masahiro: "Crystal structures and electrical conductivities of cation radical salts of a tellurium-containing donor : 3, 4-dimethylantbra[1, 9-c, d : 4, 10-c′d′]bis[1, 2]ditellurole" J.Chem.Soc., Chem.Commun.6. 593-594 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Aso Yoshio: "3, 3-Thienylene-ethynylene oligomers" Phosphorus, Sulfur, and Silicon and the Related Elements. 120 & 121. 417-418 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Takimiya Kazuo: "Syntheses, Unique Strained Molecular Structures, and Unusual Transannular Electronic Interactions of a Series of Crisscross-Overlapped Tetrathiafulvalenophanes" The Journal of Organic Chemistry. 62(16). 5567-5574 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] 安蘇 芳雄: "複数のチエニル基を有するテトラチアフルバレンの合成と性質" 日本化学会誌. 11. 777-783 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Takimiya Kazuo: "Syntheses and Properties of 11, 11, 12, 12-Tetracyano-2, 6-anthraquinodimethane(TANT) and Its 9, 10-Dichloro Derivative as Novel Extensive Electron Acceptors" Bull.Chem.Soc.Jpn.71(6). 1431-1435 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Arai Emiko: "Novel Stable Metallic Salts on a Donor Molecule Containing peri-Ditellurium Bridges, TMTTeN" Inorganic Chemistry. 37(12). 2850-2851 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Ogura Fumio: "Handbook of Organic Conductive Molecules and Polymers. (ed.by II.S.Nalwa), Vol.1, Chapter 4" John Wiley & Sons Ltd., 20 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Ogura Fumio: "Organoselenium Chemistry. A Practical Approach. (ed. by T.G.Back), Chapter 14. Preparation of Organic Conductors" Oxford University Press in press, (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Masahiro Nakata, et al.: "Crystal Structures and electrical conductivites of cation radical salts of a tellurium-containing donor : 3,4-dimethyl- anthra [1,9-cd : 4,10-c'd'] bis [1,2] ditellurole." J.Chem.Soc., Chem.Commun.No.6. 593-594 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshio Aso, et al.: "3,4'-Thienylene-ethynylene Oligomers." Phosphorus, Sulfur, and Silicon and the Related Elements. 120 & 121. 417-418 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kazuo Takimiya, et al.: "Syntheses, Unique Strained Molecular Structures, and Unusual Transannular Electronic Interactions of a Seies of Crisscross-Overlapped Tetrathiafulvalenophanes" J.Org.Chem. 62 (16). 5567-5574 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Yoshio Aso, et al.: "Syntheses and Properties of Multithienyl-Substituted Tetrathiafulvalenes." Journal of the Chemical Society of Japan, Chemistry and Industrial Chemistry. No.11. 777-783 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Kazuo Takimiya, et al.: "Syntheses and Properties of 11,11,12,12-Tetracyano-2,6-anthraquinodimethane (TANT) and Its 9,10-Dichloro Derivative as Novel Extensive Electron Acceptors." Bull.Chem.Soc.Jpn.71 (6). 1431-1435 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Emiko Arai, et al.: "Novel Stable Matallic Salts on a Donor Molecule Containing peri-Ditellurium Bridges, TMTTeN." Inorganic Chemistry. 37 (12). 2850-2851 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Fumio Ogura et al.: Conductive Hetero-TCNQs.Handbook of Organic Conductive Molecules and Polymers. (ed.by H.S.Nalwa) , Vol.1, Chapter 4. John Wiley & Sons, 229-248 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Fumio Ogura et al.: Preparation Organic Conductors. Organoselenium Chemistry.A.Practical Approach. (ed.by T.G.Back) , Chapter 14. Oxford University Press, 257-277 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Nakata Masahiro(中田 将裕): "Crystal structures and electrical conductivities of cation radical salts of a tellurium-containing donor:3,4-dimethylanthra[1,9,c,d,4,10-c'd']bis[1,2]ditellurole" J.Chem.Soc.,Chem.Commun.6. 593-594 (1997)

    • Related Report
      1998 Annual Research Report
  • [Publications] Aso Yoshio(安蘇 芳雄): "3,3-Thienylene-ethynylene oligomers" Phosphorus,Sulfur,and Silicon and the Related Elements. 120 & 121. 417-418 (1997)

    • Related Report
      1998 Annual Research Report
  • [Publications] Takimiya Kazuo(瀧宮 和男): "Syntheses,Unique Strained Molecular Structures,and Unusual Transannular Electronic Interactions of a Series of Crisscross-Overlapped Tetrathiafulvalenophanes" The Journal of Organic Chemistry. 62(16). 5567-5574 (1997)

    • Related Report
      1998 Annual Research Report
  • [Publications] 安蘇 芳雄: "複数のチエニル基を有するテトラチアフルバレンの合成と性質" 日本化学会誌. 11. 777-783 (1997)

    • Related Report
      1998 Annual Research Report
  • [Publications] Takimiya Kazuo(瀧宮 和男): "Syntheses and Properties of 11,11,12,12-Tetracyano-2,6-anthraquinodimethane(TANT)and Its 9,10-Dichioro Derivative as Novel Extensive Electron Acceptors" Bull.Chem.Soc.Jpn.71(6). 1431-1435 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Arai Emiko(新井 恵美子): "Novel Stable Metallic Salts on a Donor Molecule Containing peri-Ditellurium Bridges,TMTTeN" Inorganic Chemistry. 37(12). 2850-2851 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Ogura Fumio(小倉 文夫): "Handbook of Organic Conductive Molecules and Polymers.(ed.by H.S.Nalwa),Vol.1,Chapter 4" John Wiley & Sons Ltd., 20 (1997)

    • Related Report
      1998 Annual Research Report
  • [Publications] Ogura Fumio(小倉 文夫): "Organoselenium Chemistry.A Practical Approach.(ed.by T.G.Back),Chapter 14.Preparation of Organic Conductors" Oxford University Press(in press), 20 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Nakata Masahiro(中田 将裕): "Crystal structures and electric conductivities of cation-radical salts of a tellurium containing donor 3,4-dimethylanthra[1,9-cd:4,10-c'd']bis[1,2]ditellurole" J.Chem.Soc.,Chem.Commun.6. 593-594 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Aso Yoshio(阿蘇 芳雄): "3,3-Thienylene-ethynylene oligomers" Phosphorus,Sulfur,and Silicon and the Related Elements. 120 & 121. 417-418 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Takimiya Kazuo(瀧宮 和男): "Syntheses,Unique Strained Molecular Structures,and Unusual Transannular Electronic Interactions of a Series of Crisscross-Overlapped Tetrathiaful valenophanes" The Journal of Organic Chemistry. 62(16). 5567-5574 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 阿蘇 芳雄: "複数のエチニル基を有するテトラチアフルバレンの合成と性質" 日本化学会誌. 11. 777-783 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Ogura Fumio(小倉 文夫): "Handbook of Organic Conductive Molecules and Polymers.(ed by H.S.Nalwa),Vol.1.Chapter4" John Wiley & Sons Ltd., 20 (1997)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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