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A new synthesis and properties of tetrabenzoporphyrin and phthalocyanine

Research Project

Project/Area Number 18550036
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

ONO Noboru  Ehime University, Graduate School of Science and Technology Department of Chemistry, Professor (40093215)

Project Period (FY) 2006 – 2007
Project Status Completed (Fiscal Year 2007)
Budget Amount *help
¥3,840,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥240,000)
Fiscal Year 2007: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2006: ¥2,800,000 (Direct Cost: ¥2,800,000)
KeywordsOrganic Semiconductor / Thermal reaction / Solution process / Porphyrin / Phthalocyanine / Field effect transistor / 太陽電池 / 有機薄膜トランジスタ / 塗布
Research Abstract

Tetrabennzoprphyrin (TBP) and phthalocyanine (Pc) are organic semiconductors with planar structure, and they have been used for various electronic devices under vacuum deposition. We have succeeded in preparing thin films of such pigments by solution process. Porphyrins fused with bicycle[2.2.2]octadiene (BCOD) are converted into TBP via thermal reaction. Using this procedure, thin films of TBP are prepared by spin coating of soluble precursors followed by thermal treatment. which show good performance of field effect transistor (FET). The introduction of dimethyl groups increases the solubility of the precursors, which enables the spin coating by using hydrocarbon solvents. In a similar way, soluble precursors of Pc and naphtha locyanine (Nc) are prepared, from which FET of Pc and Nc are prepared by a solution process.

Report

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

    (34 results)

All 2008 2007 2006 Other

All Journal Article (18 results) (of which Peer Reviewed: 8 results) Presentation (8 results) Book (3 results) Remarks (2 results) Patent(Industrial Property Rights) (3 results)

  • [Journal Article] Organic semiconductors based on small molecules with thermally or photochemically removal groups2008

    • Author(s)
      H. Yamada, T. Okujima, N. Ono
    • Journal Title

      Chem. Commun (In press)

    • 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] Organic semiconductors based on small molecules with Thermally or photochemically removal groups2008

    • Author(s)
      H. Yamada, T. Okujima, N. Ono
    • Journal Title

      Chem Commun (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Supramolecules based on porphyrins2008

    • Author(s)
      H. Yamada, T. Okujima, N. One
    • Journal Title

      Springer

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Barton-Zard pyrrole synthesis and its application to synthesis of porphyrins,poly pyrroles,and dipyrromethene dyes2008

    • Author(s)
      N. Ono
    • Journal Title

      Heterocycles 74

      Pages: 243-284

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Organic semiconductors based on small molecules with thermally orphotochemically removable groups2008

    • Author(s)
      H. Yamada, T. Okujima, and N. Ono
    • Journal Title

      Chem. Commun (In press)

      Pages: 19-19

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Polycrystalline tetrabenzoporpjhyrin organic field-effect transistor with Nanostructured channels2007

    • Author(s)
      P. B. Shea, C. Chen, J. Kanicki, L. R. Pattison, P. Petroff, H. Yamada, N. Ono
    • Journal Title

      Appl. Phys. Lett 90

    • 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] Solution-processed polycrystalline copper tetrabenzoporphyrin thin film transistors2007

    • Author(s)
      P. B. Shea, M. Kawano, C. Chen, P. Petroff, D. C. Martin, H. Yamada, N. Ono, J. Kanicki
    • Journal Title

      Synth. Metal 157

      Pages: 190-197

    • 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] Polycrystalline tetrabenzoporphyrin organic field effect transistors with Nanostructured channelsV2007

    • Author(s)
      P. B. shea, C. Chen, J. Kanicki, L. R. Pattison, P. Petroff, H. Yamada, N. Ono
    • Journal Title

      Appl. Phys. Lett 90

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Solution processed polycrystalline copper tetrabenzoporphyrin thin film transistors2007

    • Author(s)
      PB. Shea, M. Kawano, C. Chen, P. Petroff, D. C. Martin, H. Yamada, N. Ono, J. Kanicki
    • Journal Title

      Synth. Metal 157

      Pages: 190-197

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Polycrystalline tetrabenzoporphyrin organic field-effbct transistors withnanostructuired channels2007

    • Author(s)
      P. B. Shea, C. Chen, J. Kanicki, L. R. Pattison, P. Petroff, H. Yamada, N. Ono
    • Journal Title

      Appl.Phys.Lett 90

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Solution-processed polycrystalline-copper tetrabenzoporphyrins thin-film transistors2007

    • Author(s)
      P. B. Shea, L. R. Pattison, M. KawanO, C. Chen, J. Chen, P. Petroff, D. C. Martin, H. Yamada, N. Ono, J. Kanicki
    • Journal Title

      Synth.Metals 157

      Pages: 190-197

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of phthalocyanine fused with bicycle[2.2.2]octadienes and thermal conversion into naphthalocyanine2007

    • Author(s)
      T. Akiyama, A. Hirao, T. Okujima, H. Yamada, H. Uno, and N. Ono
    • Journal Title

      Heterocycles 74

      Pages: 835-843

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Novel one pot synthesis of 5-alkenyl-15-alkybylporphyrins and their derivatisation to a buttadiyne benzoporphyrin dimers2006

    • Author(s)
      Yamada.H, Kushibe.K, Okujima.T, Uno.H, Ono.N.
    • Journal Title

      Chem. Commun

      Pages: 383-385

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Effective photochemical synthesis of an air-stable anthracene-based organic semiconductor from its diketone precursor2006

    • Author(s)
      Yamada.H, Kawamura.H, Okujima.T, Uno.H, Ono.N.
    • Journal Title

      Tetrahedron Lett 47

      Pages: 7501-7504

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Solution-processed nickel tetrabenzoporphyrin thin-film transistors2006

    • Author(s)
      Shea, P.B., Kanicki, J., Pattison, L.R., Petroff, P., Kawano, M., Yamada, H., Ono, N.
    • Journal Title

      J. Appl. Phys 100

      Pages: 34501-34507

    • Related Report
      2006 Annual Research Report
  • [Journal Article] A New Synthesis of Tetra(quinoxalino)tetraazaporphyrin by retro Diels-Alder Reaction of a Soluble Precursor2006

    • Author(s)
      Okujima, T., Kikuchi, M., Yamada, H., Uno, H., Ono, N.
    • Journal Title

      J. Porphyrins, Phthalocyanines 10

      Pages: 1197-1121

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Synthesis of 4,7-Dihydro-2H-isoindole Derivatives via Diels-Alder Reaction of Tosylacetylene2006

    • Author(s)
      Okujima, T., Jin, G., Hashimoto, Y, Yamada, H., Uno, H., Ono, N.
    • Journal Title

      Heterocycles

      Pages: 619-626

    • Related Report
      2006 Annual Research Report
  • [Journal Article] A synthesis of acenaphthobenzoporhyrin and fluororanthobenzoporhyrin2006

    • Author(s)
      Okujima.T, Komobuchi.N, Uno, H, Ono, N.
    • Journal Title

      Heterocycles 67

      Pages: 255-267

    • Related Report
      2006 Annual Research Report
  • [Presentation] ポルフィリン系低分子化合物を用いた塗布型有機半導体の開発2007

    • Author(s)
      小野 昇
    • Organizer
      第37回構造有機化学討論会
    • Place of Presentation
      北海道大学
    • Year and Date
      2007-10-28
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Synthesis and Properties of Pyrroles and Porphyrins Fused with Polycyclic Aromatic Hydrocarbons2007

    • Author(s)
      奥島 鉄雄・中村 純・山田 容子・小野 昇
    • Organizer
      12^<th> Intenational Symposium on Novel Aromatic Compounds
    • Place of Presentation
      淡路島(淡路夢舞台国際会議場)
    • Related Report
      2007 Annual Research Report
  • [Presentation] Photochemical synthesis of acene compounds for organic electronics from diketone precursors2007

    • Author(s)
      Hiroko Yamada, Yuko Yamashita, Hiroo Kawano, Noboru Ono
    • Organizer
      XXIII International Conference on Photochemistry
    • Place of Presentation
      Cologne,Germany
    • Related Report
      2007 Annual Research Report
  • [Presentation] Synthesis and photochemistry ofdiketone precursor of tetracene2007

    • Author(s)
      Yuko Yamashita, Hiroko Yamada, Noboru Ono
    • Organizer
      XXIII International Conference on Photochemistry
    • Place of Presentation
      Cologne,Germany
    • Related Report
      2007 Annual Research Report
  • [Presentation] 逆Diels-Alder反応を用いたペリレン類縮環型ポルフィリンの合成と物性2007

    • Author(s)
      中村 純・奥島 鉄雄・山田 容子・小野 昇
    • Organizer
      第37回構造有機化学討論会
    • Place of Presentation
      札幌(北海道大学)
    • Related Report
      2007 Annual Research Report
  • [Presentation] 共役拡張型シアノポルフィリン類の合成と物性2007

    • Author(s)
      大石 章博・平尾 敦子・奥島 鉄雄・山田 容子・小野 昇
    • Organizer
      第37回構造有機化学討論会
    • Place of Presentation
      札幌(北海道大学)
    • Related Report
      2007 Annual Research Report
  • [Presentation] ジアルキルテトラベンゾポルフィリン金属錯体の合成と物性2007

    • Author(s)
      真田 桂子・奥島 鉄雄・山田 容子・小野 昇
    • Organizer
      第37回構造有機化学討論会
    • Place of Presentation
      札幌(北海道大学)
    • Related Report
      2007 Annual Research Report
  • [Presentation] イソチアナフテンオリゴマー-フラーレン連結化合物の合成と物性2007

    • Author(s)
      竹田 佳代, 山田 容子, 小野 昇
    • Organizer
      第37回構造有機化学討論会
    • Place of Presentation
      札幌(北海道大学)
    • Related Report
      2007 Annual Research Report
  • [Book] Supramolecules based on porphyrins in Heterocyclic Supramolecules2008

    • Author(s)
      H. Yamada, T. Okujima, N. Ono
    • Total Pages
      37
    • Publisher
      Springer
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Book] Supramolecules Based on Molecules(章)in"Heterocyclic Supramolecules I"Ed.by K.Matsumoto2008

    • Author(s)
      Hiroko Yamada, Tetsuo Okujima, Noboru Ono
    • Total Pages
      37
    • Publisher
      Springer
    • Related Report
      2007 Annual Research Report
  • [Book] 最新 機能性色素大全集 第12章 有機トランジスタ2007

    • Author(s)
      小野 昇
    • Total Pages
      20
    • Publisher
      技術情報協会
    • Related Report
      2006 Annual Research Report
  • [Remarks] 「研究成果報告書概要(和文)」より

    • URL

      http://kenqweb.office.ehimeu.ac.jp/Profiles/0010/0000321/profile.html

    • Related Report
      2007 Final Research Report Summary
  • [Remarks]

    • URL

      http://kenqweb.office.ehime-u.ac.jp/Profiles/0010/0000321/profile.html

    • Related Report
      2007 Annual Research Report
  • [Patent(Industrial Property Rights)] ビシクロポルフィリン化合物、ビシクロピロール化合物の製造方法、有機半導体の製造方法2007

    • Inventor(s)
      小野 昇, 奥島 鉄男, 荒牧 晋司
    • Industrial Property Rights Holder
      愛媛大学三菱化学
    • Industrial Property Number
      2007-012720
    • Filing Date
      2007-01-23
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 半導体素子の製造方法2007

    • Inventor(s)
      桝本 茜, 菊池 憲裕, 小野 昇, 宇野 英満, 中島 容子
    • Industrial Property Rights Holder
      キャノン株式会社 国立大学法人愛媛大学
    • Filing Date
      2007-08-31
    • Related Report
      2007 Annual Research Report
  • [Patent(Industrial Property Rights)] 半導体素子の製造方法2006

    • Inventor(s)
      桝本 茜, 小野 昇, 宇野 英満, 中島 容子
    • Industrial Property Rights Holder
      キャノン株式会社, 国立大学法人愛媛大学
    • Industrial Property Number
      2006-352555
    • Filing Date
      2006-12-27
    • Related Report
      2006 Annual Research Report

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

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