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Anion Sensing by Fluorescent Expanded Calixpyrroles.

Mariia Pushina1, Petr Koutnik1, Ryuhei Nishiyabu2

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Chemistry (Weinheim an Der Bergstrasse, Germany)
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New fluorescent macrocycles, calix[2]benzo[4]pyrroles, show surprising efficiency in sensing dicarboxylate anions. Their cross-reactivity enabled a microchip array for precise analyte classification and quantification.

Keywords:
anion sensingcarboxylatesexpanded calixpyrrolesfluorescencemacrocycles

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Area of Science:

  • Supramolecular Chemistry
  • Analytical Chemistry
  • Organic Synthesis

Background:

  • Calixpyrrole macrocycles are known for anion binding.
  • Fluorescent sensors offer sensitive detection methods.
  • Tailoring macrocycle size is crucial for selective anion recognition.

Purpose of the Study:

  • Synthesize novel fluorescent calix[2]benzo[4]pyrroles.
  • Investigate their anion-binding properties, focusing on dicarboxylates.
  • Compare their sensing capabilities with traditional calix[4]pyrroles.

Main Methods:

  • Knoevenagel condensation for synthesis.
  • NMR, UV/Vis, and fluorescence spectroscopy for binding studies.
  • Microchip-based array with linear regression for analysis.

Main Results:

  • Successfully synthesized fluorescent calix[2]benzo[4]pyrroles.
  • Calix[4]pyrroles demonstrated comparable or superior dicarboxylate sensing.
  • Developed a highly cross-reactive sensor array for 18 analytes with 100% classification.
  • Quantitative analysis of oxalate and malonate with <2% error.

Conclusions:

  • Expanded calixpyrrole macrocycles are effective fluorescent anion sensors.
  • Calix[4]pyrroles remain highly competitive for dicarboxylate sensing.
  • Microchip arrays utilizing cross-reactive sensors provide a powerful platform for complex analyte mixtures.