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STUDY OF DUAL FLUORESCENCE OF FLUORINATED BENZOAZOLES AND THEIR APPLICATION AS CHEMOSENSORS

Research Project

Project/Area Number 14550811
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 有機工業化学
Research InstitutionSEIKEI UNIVERSITY

Principal Investigator

TANAKA Kiyoshi  SEIKEI UNIVERSITY, FACULTY OF ENGINEERING, PROFESSOR, 工学部, 教授 (40138540)

Project Period (FY) 2002 – 2004
Project Status Completed (Fiscal Year 2004)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2004: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2003: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2002: ¥2,200,000 (Direct Cost: ¥2,200,000)
Keywordsbenzoxazole / imidazopyridine / fluorophore / chemosensor / metal cation recognition / excited state intramolecular proton transfer / Stokes shift / hydroxyfluorophenyl / 多重蛍光 / 多重分子センサー / ヒドロキシフルオロフェニル基 / 緑色蛍光 / フルオロフェニル基 / ベンゾチアゾール / バンゾオキサゾール / 二重蛍光 / フッ素化ヘテロ環
Research Abstract

2-(2-Hydroxyfluorophenyl)benzoxazole having imidazole moiety 1 is synthesized and its dual fluorescence is applied to a multiple chemosensor for metal cations ; addition of Al^<3+>, Zn^<2+>, or Mg^<2+> causes the green emission together with slight blue emission in chloroform-acetonitrile, the enhancement ratio of both emissions being dependent on the captured metal cations. The green emission is ascribed to the ligation of the metal cation on the imidazole nitrogen atom, and the resulting positive character of nitrogen atom is inductively communicated to the hydroxyl group, to recover its hydrogen bonding ability leading to the excited state intramolecular proton transfer (ESIPT) process. The green emission is found with 2-(2-aminofluorophenyl)benzoxazole derivatives, particularly with 2-(2-pentafluorobenzamido-3,4,5,6- tetrafluorophenyl)benzoxazole. The green emission is enhanced in nonpolar solvents, resulting in the considerably large Stokes shift. Moreover, in place of the benzoxazole ring system, the corresponding fluorophores constituted by imidazopyridine ring system are synthesized and their recognition ability is disclosed. 2-(3,4,5,6-Tetrafluoro-2-hydroxyphenyl)imidazopyridine (2) is demonstrated to have a high potential as a fluorescent chemosensor for a metal cation, which can signal a distinct wavelength emission corresponding to each captured metal cation. When 2 senses Zn^<2+> cation in acetonitrile solution, it causes the blue emission around 430 nm wavelength; and when 2 senses Al^<3+> and Hg^<2+>, it signals the sky blue emission around 370 nm wavelength. This ability is attributable to the complex in which the attached hydroxyl groups and the coordinated water molecules on the metal cation link via the hydrogen bondings to the 1-nitrogen atom and to the 2-fluorine atom of 2.

Report

(4 results)
  • 2004 Annual Research Report   Final Research Report Summary
  • 2003 Annual Research Report
  • 2002 Annual Research Report
  • Research Products

    (2 results)

All 2002

All Journal Article (2 results)

  • [Journal Article] Novel Fluorescent 2-(2-Aminofluorophenyl)benzoxazoles : Syntheses and Photophysical Properties2002

    • Author(s)
      Kiyoshi Tanaka
    • Journal Title

      J.Heterocyclic Chem. 39・6

      Pages: 1299-1304

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Novel Fluorescent 2-(2-Aminofluorophenyl)benzoxazoles : Syntheses and Photophysical Properties2002

    • Author(s)
      Kiyoshi Tanaka
    • Journal Title

      J.Heterocyclic Chem. 39(6)

      Pages: 1299-1304

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary

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Published: 2002-04-01   Modified: 2016-04-21  

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