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A Chemosensor Bearing Sulfonyl Azide Moieties for Selective Chromo‐Fluorogenic Hydrogen Sulfide Recognition in Aqueous Media and in Living Cells
Author(s) -
SantosFigueroa Luis E.,
de laTorre Cristina,
El Sayed Sameh,
Sancenón Félix,
MartínezMáñez Ramón,
Costero Ana M.,
Gil Salvador,
Parra Margarita
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301514
Subject(s) - chemistry , photochemistry , azide , hydrogen sulfide , sulfonyl , naked eye , fluorescence , aqueous solution , acetonitrile , sulfide , sulfur , organic chemistry , chromatography , detection limit , alkyl , physics , quantum mechanics
A simple chemodosimeter based on a sulfonyl azide dye ( 1 ‐Az), which displayed a highly selective response toward hydrogen sulfide anion in mixed aqueous media, was synthesised and characterised. Addition of hydrogen sulfide to acetonitrile/HEPES 1:1 solutions of 1 ‐Az induced a clear colour change from red‐orange to yellow, which was easily detected by the naked eye, and by an enhancement in the emission intensity. Other common anions, thiol‐containing biomolecules and oxidants did not induce any noticeable colour or fluorescence modulation in the probe. The chemodosimeter also showed a good sensitivity, with limits of detection of 11.91 and 0.63 μ M by using UV/Vis or fluorescence measurements, respectively. Moreover, 1 ‐Az could be used for real‐time fluorescence imaging of intracellular HS – at micromolar concentrations.