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Development of Novel Organic p-Electronic Molecules and Their Application to Color Materials

Research Project

Project/Area Number 18550174
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic industrial materials
Research InstitutionChiba University

Principal Investigator

OGURA Katsuyuki  Chiba University, Graduate School of Engineering, Professor (60114253)

Co-Investigator(Kenkyū-buntansha) MATSUMOTO Shoji  Chiba University, Graduate School of Engineering, Assistant Professor (50302534)
Project Period (FY) 2006 – 2007
Project Status Completed (Fiscal Year 2007)
Budget Amount *help
¥4,060,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥360,000)
Fiscal Year 2007: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2006: ¥2,500,000 (Direct Cost: ¥2,500,000)
KeywordsMetallic Luster / Tricyanoethenyl Derivatives / Organic π-System / Thin Film / Electron-Conducting / 電気伝導性
Research Abstract

This research aimed the development of various functional materials (for example color material) having tricyanoethenyl (TCE) group, which makes neutral organic π-electronic systems interact with each others intermolecularly. In 2007, we investigated the origin of the metallic luster induced by 1-aryl-2- (2-thienyl) -5- (5-tricyano-2-thienyl) pyrrole (1) crystals as well as the development of novel molecules having TCE groups that form thin film with metallic luster and, as a result, the following fruitful results were gained. 1) Theoretical Investigation of the origin of the metallic luster. The relationship between the arrangement of the π-electronic molecules (1) and the metallic luster were investigated by the use of plane-polarized light that was irradiated on each plane of the single crystal of 1, elucidating that successive arrangement of the π-molecules in such a manner that tricyanoethenyl group interacts with pyrrole π-system intermolecularly. This conclusion was also supported by the theoretical calculation with the ab initio molecular orbital method (B3LYP/6-31G(d)). 2) Development of Stable Metal-lustrous thin films by the Use of TCE Groups Last year, we found that the compounds having two or more N-[4- (tricyanoethenyl) pheny]anilino (TCPA) groups forms a thin film with metallic luster. Furthermore, we have been investigating what kind of compound having TCPA groups can give a stable thin film with gold-like luster. As a result, it was elucidated that methyl 3, 5-dimethylbenzoate having TCPA at the methyl groups and methyl benzoate having TCPA groups at the 3- and 5-positions form a stable thin film with metallic luster. Furthermore, the benzoate ester that has two TCPA groups at 3- and 5-positions was found to form a stable thin film with metallic luster.

Report

(3 results)
  • 2007 Annual Research Report   Final Research Report Summary
  • 2006 Annual Research Report
  • Research Products

    (18 results)

All 2008 2007 2006

All Journal Article (13 results) (of which Peer Reviewed: 7 results) Presentation (5 results)

  • [Journal Article] Convenient synthesis of 3, 3, 3-trifluoropropanoic acid by hydrolytic oxidation of 3, 3, 3-trifluoropropanal dimethyl acetal2008

    • Author(s)
      Takeo Komata
    • Journal Title

      Journal of Fluorine Chemistry 129

      Pages: 35-39

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] 「研究成果報告書概要(和文)」より2008

    • Author(s)
      Shoji Matsumoto
    • Journal Title

      Journal of Organic Chemistry 73

      Pages: 1726-17313

    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] Convenient synthesis of 3, 3, 3-trifluoropropanoic acid by hydrolytic oxidation of 3, 3, 3-trifluoropropanal dimethyl acetal2008

    • Author(s)
      Takeo Komata, Shinya Akiba, Kenji Hosoi, and Katsuyuki Ogura
    • Journal Title

      J. Fluorine Chem. 129(1)

      Pages: 35-39

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Novel Formation of Iodobenzene Derivatives from 1- (Methylthio)-3-tosylhexa-1, 3 -dien-5-ynes via Iodine-Induced Intramolecular Cyclization2008

    • Author(s)
      Shoji Matsumoto, Kenji Takase, and Katsuyuki Ogura
    • Journal Title

      J. Org. Chem. 73

      Pages: 1726-1731

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Convenient synthesis of 3,3,3-trifluoropropanoic acid by hydrolytic ocidation of 3,3,3-trifluoropropanal dimethyl acetal2008

    • Author(s)
      Takeo Komata
    • Journal Title

      Journal of Fluorine Chemistry 129

      Pages: 35-39

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Novel Formation of Iodobenzene Derivatives from1-(Methylthio)-3-tosyl-hexa-1,3-dien-5-ynes via Iodine-Induced Intramolecular Cyclization2008

    • Author(s)
      Shoji Mabsumoto
    • Journal Title

      Journal of Organic Chemistry 73

      Pages: 1726-1731

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The cross-aldol reaction of hexafluoroacetone (HFA) with ketones catalyzed by an acid2007

    • Author(s)
      Takeo Komata
    • Journal Title

      Journal of Fluorine Chemistry 128

      Pages: 902-909

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] The cross-aldol reaction of hexafluoroacetone (HFA) with ketones catalyzed by an acid2007

    • Author(s)
      Takeo Komata, Kei Matsunaga, Yoshiki Hirotsu, Shinya Akiba, and Katsuyuki Ogura
    • Journal Title

      J. Fluorine Chem. 128(8)

      Pages: 902-909

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] The cross-aldol reaction of hexafluoroacetone(HEA) with ketones catalyzed by an acid2007

    • Author(s)
      Takeo Komata
    • Journal Title

      Joumal of Fluorine Chemistry 128

      Pages: 902-909

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 4-(4-Pyridyl)benzoic Acid (PybenH) Dimer: An Efficient and Reasonable Design for a Long Linear Bidentate Building Block Employed in Metal-Organic Coordination Framework2006

    • Author(s)
      Ryo Sekiya
    • Journal Title

      Chemistry Letters 35

      Pages: 614-615

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
    • Peer Reviewed
  • [Journal Article] 4- (4-Pyridyl) benzoic Acid (PybenH) Dimer: An Efficient and Reasonable Design for a Long Linear Bidentate Building Block Employed in Metal-Organic Coordination Framework2006

    • Author(s)
      Ryo Sekiya, Shin-ichi Nishikiori, Katsuyuki Ogura
    • Journal Title

      Chem. Lett. 35(6)

      Pages: 614-615

    • NAID

      10019162659

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Greenish metal-lustrous organic crystals formed from 1-ary1-2-(2-thienyl)-5-(5-tricyanoetheny1-2-furyl)pyrroles.2006

    • Author(s)
      Katsuyuki Ogura
    • Journal Title

      Tetrahedron 62・10

      Pages: 2413-2419

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Formation of metal-lustrous organic crystals from 2-aryl-1-(4-methoxyphenyl)-5-(5-tricyanoethenyl-2-thienyl)pyrroles2006

    • Author(s)
      Katsuyuki Ogura
    • Journal Title

      Tetrahedron 62・11

      Pages: 2484-2489

    • Related Report
      2006 Annual Research Report
  • [Presentation] N-[p-(トリシアノエテニル)フェニル]アニリノ置換基をもつ新規π電子系化合物:金属光沢薄膜形成能に対するアルコキシ基導入効果2008

    • Author(s)
      小倉克之
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      東京都豊島区
    • Year and Date
      2008-03-29
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Novel p-electronic compounds having N- [p- tricyanoethenyl) phenyl] anilino groups: the effect of alkoxyl group on their ability to form a thin layer with metallic luster2008

    • Author(s)
      Katsuyuki Ogura, Motoki Tanaka, Motohiro Akazome, and Shoji Matsumoto
    • Organizer
      The 88th spring annual meeting of the Chemical Society of Japan
    • Place of Presentation
      Tokyo
    • Year and Date
      2008-03-29
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] N[P-(トリシアノエテニル)フェニル]アニリノ置換基をもつ新規π電子系化合物:金属光沢薄膜形成能に対するアルコキシ基導入効果2008

    • Author(s)
      小倉 克之
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      東京都豊島区
    • Year and Date
      2008-03-29
    • Related Report
      2007 Annual Research Report
  • [Presentation] 1一アリール-2-(2-チエニル)-5-[5-(トリシアノエテニル)-2-チエニル]ピロール類結晶の金属光沢発現:π電子系の配列と反射スペクトルの相関について2007

    • Author(s)
      小具健一
    • Organizer
      日本化学会第87春季年会
    • Place of Presentation
      吹田市
    • Year and Date
      2007-03-26
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Metallic luster of 1-aryl-2- (2-thienyli-5-[ 5- (tricyanoethenyl) -2-thienyl] pyrrol crystals: Relationship between the arrangement of pai-molecules and reflection spectra2007

    • Author(s)
      Ken-ich Ogu and Katsuyuki Ogura
    • Organizer
      The 87th spring annual meeting of the Chemical Society of Japan
    • Place of Presentation
      Suita
    • Year and Date
      2007-03-26
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary

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Published: 2006-04-01   Modified: 2016-04-21  

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