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Development of Novel Photo-responsive Compounds with Multi Molecular Recognition Sites

Research Project

Project/Area Number 15550118
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Functional materials chemistry
Research InstitutionOsaka Institute of Technology (2004)
Osaka University (2003)

Principal Investigator

NAKATSUJI Yohji  Osaka Institute of Technology, Faculty of Engineeirng, Progessor, 工学部, 教授 (00127268)

Co-Investigator(Kenkyū-buntansha) KIDA Toshiyuki  Osaka University, Graduate School of Engineering, Lecturer, 大学院・工学研究科, 講師 (20234297)
Project Period (FY) 2003 – 2004
Project Status Completed (Fiscal Year 2004)
Budget Amount *help
¥3,800,000 (Direct Cost: ¥3,800,000)
Fiscal Year 2004: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2003: ¥2,800,000 (Direct Cost: ¥2,800,000)
Keywordsmolecular recognition / monoazacryptand / lariat ethier / fluorescence spectroscopy / surfactant / micelle / barium ion sensor / アルカリ土類金属イオン
Research Abstract

This research deals with the selective discrimination of alkali metal and alkaline earth metal cations by novel photo-responsive host molecules. -The results obtained through this work are summarized as follows.
1)Two types of double-armed lariat ethers with pyrene moieties at each end of two sidearms were synthesized and their complexation properties toward alkali metal and alkaline earth metal cations were examined by fluorescence spectroscopy. Pyrene excimer emission decreased accompanied by an increase in monomer emission upon metal ion complexation. This finding is ascribed to the change of the spatial distance of two pyrene rings by movement suppression of both the crown ring and one of the two sidearms based on complexation with the metal cation The selectivity for alkaline earth metal cations was highly dependent on the fitness of the host cavity and the guest size.
2)Novel monoazacryptand-type fluorescent indicators with a pyrene ring were described and their fluorescent charact … More eristics in the presence of alkali metal and alkaline earth metal cations in waterwere examined. The detection of metal cations was performed by the change of the fluorescence intensity of host compounds based on PET mechanism. In aqueous solution, the fluorophore showed little fluorescence upon the addition of Ba^<2+> because of the very weak complexation ability with Ba^<2+>, but the coexistence of Triton X-100 micelles enabled the fluorophore to detect Ba^<2+> with very high sensitivity and selectivity. Moreover, the complexation behavior between the monoazacryptand-type fluorophore and Ba^<2+> was utilized as anew pyrene-functionalized probe for CMC determination. From a comparison of the CMC values obtained by the PET method versus the CMC values obtained by conventional fluorescent methods utilizing DPH, ANS and pyrene probes as well as the literature values, one can conclude that this PET method was useful for the CMC determination of various nonionic and anionic surfactants, and for the CMC determination of nonionic surfactants with arvery low CMC, and was more effective than any other fluorescent method. This notable achievement may be due to the high sensitivity of the pyrene ring, the higher solubility of the probe (due to the presence of the cryptand functionality) over pyrene, and a drastic change in the fluorescence intensity based on the PET mechanism Less

Report

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

    (10 results)

All 2005 2004 Other

All Journal Article (9 results) Publications (1 results)

  • [Journal Article] Fluorometric Sensing of Alkali Metal and Alkaline Earth Metal Cations by Novel Photosensitive Monoazacryptand Derivatives in Aqueous Micellar Solutions2005

    • Author(s)
      Nakahara, Yoshio
    • Journal Title

      Org.Biomol.Chem. 3

      Pages: 1787-1794

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Fluorometric Sensing of Alkali Metal and Alkaline Earth Metal Cations by Novel Photosensitive Monoazacryptand Derivatives in Aqueous Micellar Solutions2005

    • Author(s)
      Yoshio Nakahara, Toshiyuki Kida, Yohji Nakatsuji, Mitsuru Akashi
    • Journal Title

      Org.Biomol.Chem. 3

      Pages: 1787-1794

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] A novel fluorescent indicator for Ba^<2+> in aqueous micellar solutions2004

    • Author(s)
      Nakahara, Yoshio
    • Journal Title

      Chemical Communications 2004

      Pages: 224-225

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis of Double-armed Lariat Ethers with Pyrene Moieties at Each End of Plural Sidearms and Their Fluorescence Properties in the Presence of Alkali Metal and Alkaline Earth Metal Cations2004

    • Author(s)
      Nakahara, Yoshio
    • Journal Title

      Journal of Organic Chemistry 69

      Pages: 4403-4411

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] A Novel Fluorescent Indicator for Ba^<2+> in Aqueous Micellar Solutions2004

    • Author(s)
      Yoshio Nakahara, Toshiyuki Kida, Yohji Nakatsuji, Mitsuru Akashi
    • Journal Title

      Chem.Commun.

      Pages: 224-225

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis of Double-Armed Lariat Ethers with Pyrene Moieties at Each End of Two Sidearms and Their Fluorescence Properties in the Presence of Alkali Metal and Alkaline Earth Metal Cations2004

    • Author(s)
      Yoshio Nakahara, Toshiyuki Kida, Yohji Nakatsuji, Mitsuru Akashi
    • Journal Title

      J.Org.Chem. 69

      Pages: 4403-4411

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis of Double-armed Lariat Ethers with Pyrene Moieties at Each End of Plural Sidearms and Their Fluorescence Properties in the Presence of Alkali Metal and Alkaline Earth Metal Cations2004

    • Author(s)
      Nakahara, Yoshio
    • Journal Title

      Journal of Organic Chemistry 69・13

      Pages: 4403-4411

    • Related Report
      2004 Annual Research Report
  • [Journal Article] A New Fluorescence Method for the Determination of the Critical Micelle Concentration by Photosensitive Monoazacryptand Derivatives

    • Author(s)
      Nakahara, Yoshio
    • Journal Title

      Langmuir 印刷中

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] A New Fluorescence Method for the Determination of the Critical Micelle Concentration by Photosensitive Monoazacryptand Derivatives

    • Author(s)
      Yoshio Nakahara, Toshiyuki Kida, Yohji Nakatsuji, Mitsuru Akashi
    • Journal Title

      Langmuir (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Publications] Nakahara, Yoshio: "A novel fluorescent indicator for Ba^<2+> in aqueous micellar solutions"Chemical Communications. 2004・2. 224-225 (2004)

    • Related Report
      2003 Annual Research Report

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

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