Reactivity-based detection of nitrite ion: Rapid colorimetric and fluorometric response down to nM level

Recent developments in our lab provided significant insight into the structure–reactivity relationship between electronic properties and the detection of nitrite ions. By fine-tuning electron-withdrawing and electron-donating power, the sulfonamide group on aniline moiety was found to be the fastest nitrite probe among the first generation of probe molecules. Based on our understanding of the detection mechanism, our attention was moved to additional modification by installing stronger electron-donating groups on the azo-coupling partner. Accordingly, the bis methoxy group version of the probe molecule was prepared. It showed clean conversion from the probe to the benzo[c]cinnoline product and excellent linear response to very low levels of nitrite ions. Proton NMR and high-resolution mass spectrometer captured the reaction between the probe molecule and nitrite ions. As the reaction with nitrite ion triggers diazonium intermediate formation followed by intramolecular cyclization, both absorption and emission property changes were monitored as the signal readout to assay nitrite ion. In this report, our design principle of a probe molecule and its performance in colorimetric and fluorimetric responses will be discussed. In addition, the low detection limit achieved by leveraging chromatographic separation and assaying by the mass detector will be discussed.

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Work Title Reactivity-based detection of nitrite ion: Rapid colorimetric and fluorometric response down to nM level
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Open Access
Creators
  1. Jiyoung Jung
Keyword
  1. Nitrosamines
  2. Nitrite ion
  3. Griess reagent
  4. Chromatography
  5. Mass spectrometry
License In Copyright (Rights Reserved)
Work Type Article
Publisher
  1. Tetrahedron Letters
Publication Date June 13, 2024
Publisher Identifier (DOI)
  1. https://doi.org/10.1016/j.tetlet.2024.155114
Deposited July 15, 2024

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  • Added 2024_Publication_Jung.pdf
  • Added Creator Jiyoung Jung
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  • Updated Keyword, Publication Date Show Changes
    Keyword
    • Nitrosamines, Nitrite ion, Griess reagent, Chromatography, Mass spectrometry
    Publication Date
    • 2024-06-23
    • 2024-06-13