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Pyrrole-Imine Macrocycle: Self-Organizing Cross-Reactive Anion Receptor and Sensor.

Austin R Sartori1, Sandra M George1, Aco Radujević1

  • 1Chemistry Department, Bowling Green State University, Bowling Green, Ohio, 43403, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 23, 2025
PubMed
Summary
This summary is machine-generated.

New flexible macrocyclic sensors can detect and identify various phosphorus oxyanions, including phosphates and phosphonates, in water using fluorescence. These sensors show high affinity for phosphonates and enable accurate quantification in unknown samples.

Keywords:
anionsfluorescenceglyphosatephosphatesphosphonatessensing

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Area of Science:

  • Supramolecular Chemistry
  • Analytical Chemistry
  • Materials Science

Background:

  • Phosphorus oxyanions are crucial in biological systems but also significant environmental pollutants.
  • Developing selective and sensitive sensors for these anions is vital for environmental monitoring and biological studies.
  • Existing methods for detecting phosphorus oxyanions can be complex and lack specificity.

Purpose of the Study:

  • To synthesize novel self-organizing macrocyclic receptor-sensors capable of detecting and distinguishing various phosphorus oxyanions.
  • To investigate the binding affinities and sensing mechanisms of these macrocycles towards different phosphorus oxyanions.
  • To develop a fluorescence-based sensing platform for the identification and quantification of phosphorus oxyanions in aqueous solutions.

Main Methods:

  • Condensation reaction to synthesize macrocyclic receptors with imine moieties and flexible ethylene units.
  • NMR titrations (including low-temperature and NOESY NMR) to elucidate anion binding interactions.
  • Incorporation of a dansyl fluorophore for fluorescence-based sensing.
  • Linear Discriminant Analysis (LDA) and Support Vector Machine (SVM) for data analysis and quantification.

Main Results:

  • The flexible macrocycles effectively accommodate a range of phosphorus oxyanions, from orthophosphate to ATP and glyphosate.
  • Fluorescence spectroscopy revealed analyte-specific changes (intensity, bandwidth, maxima position) for eleven different P-oxyanions.
  • High affinity (Kassoc ~10^6 M^-1) was observed for phosphonates (methylphosphonate, glyphosate) and other oxyanions, with negligible affinity for halides or nitrate.
  • LDA and SVM successfully classified twelve analytes (including water) and quantified phosphonate concentrations with <3.5% error.

Conclusions:

  • The developed macrocyclic receptor-sensors offer unprecedented flexibility and accommodation for diverse phosphorus oxyanions.
  • The fluorescence-based sensing platform provides a sensitive and selective method for identifying and quantifying multiple P-oxyanions in water.
  • This approach demonstrates the potential for advanced analytical tools in environmental and biological sample analysis.