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Related Experiment Videos

BODIPY-based hydroxyaryl derivatives as fluorescent pH probes.

Mukulesh Baruah1, Wenwu Qin, Nikola Basarić

  • 1Department of Chemistry, Katholieke Universiteit Leuven, 3001 Leuven, Belgium.

The Journal of Organic Chemistry
|May 7, 2005
PubMed
Summary

Seven new BODIPY dyes were synthesized and studied for their fluorescent properties. These novel dyes function as effective fluorescent pH probes in aqueous solutions, with tunable pKa values.

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Materials Science

Background:

  • Boron-dipyrromethene (BODIPY) dyes are known for their unique photophysical properties.
  • Functionalization of BODIPY core allows for tuning of spectral and sensing characteristics.

Purpose of the Study:

  • To synthesize novel BODIPY dyes with varying substituents at positions 3, 5, and 8.
  • To investigate the photophysical properties (absorption, fluorescence, Stokes shift) of these new dyes in different solvents.
  • To evaluate their potential as fluorescent pH probes in aqueous solutions.

Main Methods:

  • Synthesis of seven new BODIPY derivatives featuring phenolic/naphtholic groups and electron-donating/withdrawing substituents.
  • Spectroscopic analysis including absorption and steady-state fluorescence measurements.

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  • Evaluation of pH-dependent fluorescence changes in aqueous solutions.

    • Main Results:

    • Synthesized BODIPY dyes exhibit absorption maxima between 493-515 nm, with one exception absorbing at 570-580 nm.
    • Most dyes show small Stokes shifts (400-600 cm(-1)).
    • The synthesized dyes demonstrate significant fluorescence enhancement with increasing acidity in aqueous solutions, functioning as pH probes with pKa values from 7.5 to 9.3.

    Conclusions:

    • Novel BODIPY dyes with tunable spectral properties and pH sensitivity have been developed.
    • These compounds are promising fluorescent pH probes for aqueous environments, excitable by visible light.
    • The substitution pattern significantly influences the photophysical properties and pKa values of the BODIPY dyes.