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A novel fluorescent pH indicator for the acidic range.

S Marchesini1, S Gatt, V Agmon

  • 1Department of Biomedical Sciences and Biotechnology, University of Brescia, Italy.

Biochemistry International
|July 1, 1992
PubMed
Summary

A new pH indicator derived from lissamine-rhodamine B exhibits maximal fluorescence in acidic conditions with a pKa of 4.6. Its structure and pH-dependent fluorescence mechanism were determined using Nuclear Magnetic Resonance (NMR) spectroscopy.

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Area of Science:

  • Organic Chemistry
  • Analytical Chemistry
  • Biochemistry

Background:

  • Lissamine-rhodamine B sulfonyl chloride is a fluorescent dye.
  • Sulfonamide derivatives can exhibit pH-dependent properties.
  • Fluorescent pH indicators are valuable tools in various scientific fields.

Purpose of the Study:

  • To synthesize and characterize novel sulfonamide derivatives from lissamine-rhodamine B.
  • To investigate the pH-dependent fluorescence behavior of a specific derivative.
  • To elucidate the structure and fluorescence mechanism of the pH-sensitive compound.

Main Methods:

  • Reaction of lissamine-rhodamine B sulfonyl chloride with primary amines.
  • Spectroscopic analysis, including Nuclear Magnetic Resonance (NMR).

Related Experiment Videos

  • Fluorescence emission spectroscopy to determine pH dependence.

    • Main Results:

    • Two sulfonamide derivatives were successfully synthesized.
    • One derivative functions as a pH indicator with maximal fluorescence in the acidic range.
    • The pKa of this indicator was determined to be approximately 4.6.
    • The structure of the pH-sensitive derivative was elucidated via NMR.
    • The mechanism of pH-dependent fluorescence was explained.

    Conclusions:

    • A novel, fluorescent sulfonamide derivative of lissamine-rhodamine B acts as an effective pH indicator.
    • The study provides structural and mechanistic insights into pH-sensitive rhodamine derivatives.
    • This indicator shows potential for applications in acidic environments where precise pH monitoring is required.