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Development and Aggregation Control of Novel Delocalized Electronic Chromophores

Research Project

Project/Area Number 15350116
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

NAKAZUMI Hiroyuki  Osaka Prefecture University, Graduate School of Engineering, Professor, 工学研究科, 教授 (00109878)

Co-Investigator(Kenkyū-buntansha) YAGI Shigeyuki  Osaka Prefecture University, Graduate School of Engineering, Associate Professor, 工学研究科, 助教授 (40275277)
HYODO Yutaka  Osaka Prefecture University, Graduate School of Engineering, Assistant Professor, 工学研究科, 助手 (40360044)
Project Period (FY) 2003 – 2005
Project Status Completed (Fiscal Year 2005)
Budget Amount *help
¥15,000,000 (Direct Cost: ¥15,000,000)
Fiscal Year 2005: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2004: ¥2,900,000 (Direct Cost: ¥2,900,000)
Fiscal Year 2003: ¥11,400,000 (Direct Cost: ¥11,400,000)
KeywordsFunctional Dyes / Squarylium Dyes / Near-infrared Absorbing Dyes / Fluorescent Probes / Porphyrins / Diarylurea Skeletons / Intermolecular excitation energy transfer / Organic Solar Cell / 蛍光寿命 / ゾル-ゲル法 / 有機-無機複合薄膜 / スクリアリリウム色素 / 光誘起電子移動 / ヒト血清アルブミン / 亜鉛ポルフィリン / 双極子-カオチン相互作用 / 低反射ゲル薄膜
Research Abstract

To develop novel chromophores with controlled aggregation and molecular recognition capacities, the following synthetic approaches for new squarylium chromophores and porphyrin chromophores have been performed and their optical properties have been clarified.
1.Novel bis-squarylium fluorophores with near-infrared emissions have been prepared, in which two squarine moieties are conjugatively linked by a thiophene, oligothiophene or pyrene spacer. These dyes exhibit enhanced fluorescence by the 1:1 dye-protein complexes when bound as noncovalent labeling probes to human serum albumin and bovine serum albumin.
2.Two asymmetric squarylium dyes with red emissions exhibit significantly enhanced fluorescence and increased quantum yield by the formation of dye-protein complexes. Similar asymmetric squarylium dyes including an indoline moiety show promise as reagent capable of fluorescently labeling proteins for analysis by capillary electrophoresis with laser-induced fluorescence detection.
3.Nov … More el oligosquarylium dyes have been prepared using palladium catalyst form bromo or iodo squarylium dye, and these dyes showed a maximum absorbance between 830 and 930nm. Asymmetric squarylium dyes, as sensitizing dye for organic solar cell for harvesting energy from sunlight, have been also prepared.
4.A zinc porphyrin dimmer and zinc-(free-base) porphyrin dyad bearing two diarylurea linkers designed for binding a viologen electron acceptor were prepared. The excitation energy transfer (EET) from the zinc porphyrin to the free-base porphyrin unit was confirmed by the steady-state fluorescence emission spectroscopy. Structurally controlled zinc porphyrin-anthracene dyads were newly synthesized employing a diarylurea linkage, and the EET was investigated, focusing on the effect of the chromophoric orientation on the EET.
5.A series of zinc porphyrin receptors for a viologen substrate were prepared, in which varying numbers of diarylurea moieties. The increase in the number of the diarylurea moiety led to the increase in stability of the receptor-viologen complex, showing that the convergent dipoles set up on the porphyrin platform in the complexation. Less

Report

(4 results)
  • 2005 Annual Research Report   Final Research Report Summary
  • 2004 Annual Research Report
  • 2003 Annual Research Report
  • Research Products

    (40 results)

All 2006 2005 2004 2003 Other

All Journal Article (28 results) Book (6 results) Patent(Industrial Property Rights) (2 results) Publications (4 results)

  • [Journal Article] Molecular Recognition of Viologen by Zinc Porphyrinic Receptors with Diarylurea Sidearm. Toward Construction of a Supramolecular Electron Transfer System2006

    • Author(s)
      Masayuki Ezoe
    • Journal Title

      Tetrahedron 62・11

      Pages: 2501-2510

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Protein Labeleing with Red Squarylium Dyes for Analysis by Capillary Electrophoresis with Laser-induced Fluorescence Detection2006

    • Author(s)
      Weiying Yan
    • Journal Title

      Electrophoresis 27

      Pages: 1347-1354

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Molecular Recognition of Viologen by Zinc Porphyrinic Receptors with Diarylurea Sidearm. Toward Construction of a Supramolecular Electron Transfer System2006

    • Author(s)
      M.Ezoe, S.Yagi, H.Nakazumi, M.Itou, Y.Araki, O.Ito
    • Journal Title

      Tetrahedron 62(11)

      Pages: 2501-2510

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Protein Labeling with Red Squarylium Dyes for Analysis by Capillary Electrophoresis with Laser-induced Fluorescence Detection2006

    • Author(s)
      W.Yan, A.L.Sloat, S.Yagi, H.Nakazumi, C.Colyer
    • Journal Title

      Electrophoresis 27

      Pages: 1347-1354

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Molecular recognition of viologen by zinc porphyrinic receptors with diarylurea sidearms. Toward construction of a supramolecular electron transfer system2006

    • Author(s)
      Masayuki Ezoe
    • Journal Title

      Tetrahedron 62・11

      Pages: 2501-2510

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Protein Labeling with Red Squarylium Dyes for Analysis by Capillary Electrophoresis with Laser-induced Fluorescence Setection2006

    • Author(s)
      Weiying Yan
    • Journal Title

      Electrophoresis (印刷中)

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Near-infrared luminescent bis-squaraine dyes linked by a thiophene or pyrene spacer for noncovalent protein labeling2005

    • Author(s)
      Hiroyuki Nakazumi
    • Journal Title

      Synthetic Metals 153

      Pages: 33-36

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Intramolecular Excitation Energy Transfer in Diarylurea-Linked Zinc Porphyrin- Anthracene Dyads2005

    • Author(s)
      Masayuki. Ezoe
    • Journal Title

      Photochem.Photobiol.Sci. 4・8

      Pages: 641-646

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] 機能性色素の開発と新規分野への応用2005

    • Author(s)
      中澄博行
    • Journal Title

      触媒年鑑

      Pages: 1-10

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Annual Research Report 2005 Final Research Report Summary
  • [Journal Article] Development of Functional Squarylium Chromophores2005

    • Author(s)
      Hiroyuki Nakazumi
    • Journal Title

      Proc.2^<nd> East Asia Sym.Func.Dyes & Adv.Mater.

      Pages: 26-31

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Fluoresenc Enhancement of Squarylium Dyes by Complexation with Cyclodextrin,2005

    • Author(s)
      Miki Shirai
    • Journal Title

      Proc.2^<nd> East Asia Sym.Func.Dyes & Adv.Mater.

      Pages: 171-176

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Near-infrared Luminescent Bis-squaraine Dyes Linked Thiophene or Pyrene Spacer for Noncovalent Protein Labeling2005

    • Author(s)
      H.Nakazumi, T.Ohta, H.Etoh, T.Uno, C.L.Colyer, Y.Hyodo, S.Yagi
    • Journal Title

      Syn.Metals 153(1-3)

      Pages: 33-36

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Intramolecular Excitation Energy Transfer in Diarylurea-Linked Zinc Porphyrin- Anthracene Dyads2005

    • Author(s)
      M.Ezoe, T.Minami, Y.Ogawa, S.Yagi, H.Nakazumi, T.Matsuyama, K.Wada, H.Horinaka
    • Journal Title

      Photochem.Photobiol.Sci. 4(8)

      Pages: 641-646

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Development and New Applications of Functional Dyes2005

    • Author(s)
      H.Nakazumi
    • Journal Title

      Shokubainenkan

      Pages: 1-10

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Development of Functional Squarylium Chromophores2005

    • Author(s)
      H.Nakazumi
    • Journal Title

      Proc.2^<nd> East Asia Symposium on Functional Dyes and Advanced Materials

      Pages: 26-31

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Fluoresenc Enhancement of Squarylium Dyes by Complexation with Cyclodextrin2005

    • Author(s)
      M.Shirai, H.Nakazumi, H.Etoh, Y.Hyodo
    • Journal Title

      Proc.2^<nd> East Asia Symposium on Functional Dyes and Advanced Materials

      Pages: 171-176

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Intramolecular Excitation Energy Transfer in Diarylurea-Linked Zinc Porphyrin-Anthracene Dyads2005

    • Author(s)
      Masayuki Ezoe
    • Journal Title

      Photochem. Photobiol. Sci., 4・8

      Pages: 641-646

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Near-infrared luminescent bis-squaraine dyes linked by a thio-phene or pyrene spacer for noncovalent protein labeling2005

    • Author(s)
      Hiroyuki Nakazumi
    • Journal Title

      Synthetic Metals (印刷中)

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Sol-gel preparation of photosensitive fluorinated inorganic-organic thin films for printing plates2004

    • Author(s)
      Kazuyuki Satoh
    • Journal Title

      Thin Solid Films 460

      Pages: 217-221

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary 2004 Annual Research Report
  • [Journal Article] Sol-gel Preparation of Photosensitive Fluorinated Inorganic-organic Thin Films for Printing Plates2004

    • Author(s)
      K.Satoh, H.Nakazumi
    • Journal Title

      Thin Solid Films 460

      Pages: 217-221

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Synthesis and Photochemical Properties of Ferrocene-linked Squarylium Dimer2003

    • Author(s)
      Hiroyuki Nakazumi
    • Journal Title

      Synthetic Metals 137

      Pages: 1395-1396

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Symmetric and Asymmetric Squarylium Dyes as Noncovalent Protein Labels : a Study by Fluorimetry and Capillary Electrophoresis2003

    • Author(s)
      Frank Welder
    • Journal Title

      J.Chromatography B 793

      Pages: 93-105

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Red Luminescent Squarylium Dyes for Noncovalent HSA Labeling2003

    • Author(s)
      Hiroyuki Nakazumi
    • Journal Title

      Chemistry Letters 32・9

      Pages: 804-805

    • NAID

      10012819059

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Diarylurea-Linked Zinc Porphyrin Dimer as A Dual-Mode Artificial Receptor : Supramolecular Control of Complexation-Facilitated2003

    • Author(s)
      Shigeyuki Yagi
    • Journal Title

      J.American Chemical Society 125・14

      Pages: 4068-4069

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Synthesis and Photochemical Properties of Ferrocene-linked Squarylium Dimer2003

    • Author(s)
      H.Nakazumi, Y.Hyodo, S.Yagi
    • Journal Title

      Syn.Metals 137(1-3)

      Pages: 1395-1396

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Symmetric and Asymmetric Squarylium Dyes as Noncovalent Protein Labels : a Study by Fluorimetry and Capillary Electrophoresis2003

    • Author(s)
      F.Welder, B.Paul, H.Nakazumi, S.Yagi, C.L.Colyer
    • Journal Title

      J.Chromatogr.B. 793(1)

      Pages: 93-105

    • NAID

      10016533776

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Diarylurea-Linked Zinc Porphyrin Dimer as a Dual-Mode Artificial Receptor : Supermolecular Control of Complexation-Facilitated Photoinduced Electron Transfer2003

    • Author(s)
      S.Yagi, M.Ezoe, I.Yonekura, T.Takagishi, H.Nakazumi
    • Journal Title

      J.Am.Chem.Soc. 125(15)

      Pages: 4068-4069

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Red Luminescent Squarylium Dyes for Noncovalent HAS Labeling2003

    • Author(s)
      H.Nakazumi, CL, Colyer, K.Kaihara, Y.Hyodo, S.Yagi
    • Journal Title

      Chem.Lett. 32(9)

      Pages: 93-105

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Book] "Functional Dyes", Chapter 6, (Syntheses and application of squarylium dyes)2006

    • Author(s)
      Shigeyuki Yagi
    • Total Pages
      282
    • Publisher
      Elseveir Science
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Book] 有機デバイス用色素の基本特性,有機薄膜太陽電池の最新技術第 3章2006

    • Author(s)
      八木繁幸
    • Total Pages
      313
    • Publisher
      シーエムシー出版
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Book] Syntheses and Application of Squarylium Dyes "Functional Dyes" (ed. By S.Kim)2006

    • Author(s)
      S.Yagi, H.Nakazumi
    • Publisher
      Elseveir Science
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Book] "Functional Dyes", Chapter 6, (Syntheses and application of squarylium dyes) (pp.215-255)2006

    • Author(s)
      Shigeyuki Yagi
    • Total Pages
      282
    • Publisher
      Elseveir Science
    • Related Report
      2005 Annual Research Report
  • [Book] Basic Characterization of Organic Devices "Advanced Technology for Organic Thin Film Solar Cell" November 302005

    • Author(s)
      S.Yagi, H.Nakazumi
    • Publisher
      CMC Press
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Book] "有機薄膜太陽電池の最新技術",第3章,(有機デバイス用色素の基本特性)(pp121-127)2005

    • Author(s)
      八木繁幸
    • Total Pages
      313
    • Publisher
      シーエムシー出版
    • Related Report
      2005 Annual Research Report
  • [Patent(Industrial Property Rights)] 有機太陽電池用増感色素2005

    • Inventor(s)
      中澄 博行
    • Industrial Property Rights Holder
      大阪府立大学
    • Industrial Property Number
      2005-249491
    • Filing Date
      2005-08-30
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Patent(Industrial Property Rights)] 有機太電池用増感色素2005

    • Inventor(s)
      中澄博行
    • Industrial Property Rights Holder
      大阪府立大学
    • Industrial Property Number
      2005-249491
    • Filing Date
      2005-08-30
    • Related Report
      2005 Annual Research Report
  • [Publications] Hiroyuki Nakazumi: "Synthesis and Photochemical Properties of Ferrocene-linked Squarylium Dimer"Synthetic Metals. 137. 1395-1396 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Frank Welder: "Symmetric and Asymmetric Squarylium Dyes as Noncovalent Protein Labels : a Study by Fluorimetry and Capillary Electrophoresis"J.Chromatography B. 793. 93-105 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Hiroyuki Nakazumi: "Red Luminescent Squarylium Dyes for Noncovalent HSA Labeling"Chemistry Letters. 32・9. 804-805 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Shigeyuki Yagi: "Diarylurea-Linked Zinc Porphyrin Dimer as A Dual-Mode Artificial Receptor : Supramolecular Control of Complexation-Facilitated Photoinduced Electron Transfer"J.American Chemical Society. 125・14. 4068-4069 (2003)

    • Related Report
      2003 Annual Research Report

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Published: 2003-04-01   Modified: 2016-04-21  

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