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Squaramides for colorimetric and fluorescent anion sensing.

Jakob D E Lane1, Katrina A Jolliffe1,2,3

  • 1School of Chemistry, The University of Sydney, NSW, 2006, Australia. kate.jolliffe@sydney.edu.au.

Organic & Biomolecular Chemistry
|March 29, 2023
PubMed
Summary

New squaramide molecules were synthesized to detect anions. Molecules with a spacer showed a simple fluorescence response, enabling selective sulfate detection using a ratiometric method.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis
  • Analytical Chemistry

Background:

  • Squaramides are versatile molecules with potential applications in sensing.
  • Fluorophore-conjugated squaramides can exhibit unique optical properties.
  • Anion sensing remains a critical challenge in analytical chemistry.

Purpose of the Study:

  • To synthesize novel fluorophore-containing squaramides.
  • To investigate their fluorescent and colorimetric responses to various anions.
  • To develop a selective anion sensing system.

Main Methods:

  • Synthesis of fluorophore-conjugated and electronically insulated squaramides.
  • Spectroscopic analysis (fluorescence and colorimetric) upon anion addition.
  • Investigation of structure-property relationships in anion binding.

Main Results:

  • Conjugated squaramides showed complex fluorescence and color changes due to acidic NH protons.
  • Methylene-spacer incorporated squaramides exhibited simpler fluorescence responses.
  • A ratiometric fluorescent method was developed, with high selectivity for sulfate detection.

Conclusions:

  • Electronic insulation of fluorophores is crucial for predictable anion sensing.
  • Ratiometric fluorescence based on excimer:monomer emission offers a robust detection strategy.
  • These squaramides represent promising candidates for selective anion detection, particularly for sulfate.