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Electronic Substitution Effect on ESIPT-Driven pH and Amine Sensing: Exploring Mechanism.

Bharat Kaushik1, Annu Agarwal1, Ajeet Singh1

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Chemistry, an Asian Journal
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PubMed
Summary

New luminescent probes detect meat spoilage by sensing ammonia and biogenic amines. These probes offer a straightforward method for food quality assessment, enhancing public health safety through sensitive detection of decomposition products.

Keywords:
Amine SensingESIPTSolvatochromismSubstitution effectpH sensing

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Area of Science:

  • Analytical Chemistry
  • Materials Science
  • Food Science

Background:

  • Meat spoilage involves protein decomposition, releasing ammonia and biogenic amines (BAs).
  • Sensitive detection of BAs is crucial for evaluating meat safety and quality during storage, transit, and consumption.
  • Existing methods for BA detection may lack the simplicity and sensitivity required for widespread food quality assessment.

Purpose of the Study:

  • To design and synthesize novel luminescent-based probe molecules for detecting ammonia and biogenic amines.
  • To investigate the relationship between molecular structure, excited state-induced proton transfer (ESIPT) properties, and sensing capabilities.
  • To develop a practical method for assessing meat spoilage using these probes.

Main Methods:

  • Synthesis of three 2-(2-hydroxyphenyl) benzothiazole (HBT) derivatives with varying substituents (OMe, NO2) at the para position.
  • Evaluation of electronic properties using Hammett substituent constants to understand proton transfer dynamics.
  • Characterization of ESIPT phenomenon and pH-dependent spectral changes.
  • Quantification of ammonia and hydrazine using the synthesized probes, determining limits of detection (LOD).
  • Application of probes for strip-based detection of chicken meat spoilage in contact and non-contact modes.

Main Results:

  • Designed HBT derivatives exhibiting ESIPT phenomenon with tunable proton transfer rates influenced by substituents.
  • Demonstrated pH sensing capabilities, with the OMe-substituted compound showing prominent multi-color changes.
  • Achieved low limits of detection for ammonia (28.6 μM) and hydrazine (61.34 nM).
  • Successfully applied the probes for real-world detection of chicken meat spoilage using a strip-based assay.

Conclusions:

  • The synthesized luminescent probes offer a sensitive and straightforward approach for detecting ammonia and biogenic amines.
  • The tunable ESIPT properties allow for versatile applications in pH sensing and food spoilage detection.
  • Strip-based detection provides a practical tool for assessing meat quality and ensuring food safety.