TY - JOUR
T1 - Reactivity-based detection of nitrite ion
T2 - Rapid colorimetric and fluorometric response down to nM level
AU - Jung, Jiyoung
N1 - Publisher Copyright:
© 2024
PY - 2024/6/23
Y1 - 2024/6/23
N2 - 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.
AB - 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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U2 - 10.1016/j.tetlet.2024.155114
DO - 10.1016/j.tetlet.2024.155114
M3 - Article
AN - SCOPUS:85193840704
SN - 0040-4039
VL - 143
JO - Tetrahedron Letters
JF - Tetrahedron Letters
M1 - 155114
ER -