A Two-In-One Versatile Colorimetric Sensor for Cyanide Anion and Volatile Amines Based on 1-Hydroxyanthraquinone with Electron-Withdrawing Groups

A series of novel 2-acyloxy derivatives of 1-hydroxyanthraquinone was synthesized. The obtained dyes are of interest as optical molecular sensors for the detection of cyanide ions in aqueous environments. Interaction with CN^- results in ionization of the hydroxyl group. This study provides quantitative estimates of the efficiency of this interaction and its selectivity toward other anions in a MeCN-H₂O mixture. The hypothesis about the potential universality of such acid-base chemosensors for volatile amines was fully confirmed. The investigated dyes demonstrated sufficiently efficient interaction with the model amine (triethylamine). Polymer films containing 2-benzoylamino-1-hydroxyanthraquinone showed significant color changes in the presence of cyanide at concentrations of 10 μM and higher. These same films enabled the detection of gaseous decomposition products of fish meat (volatile amines) prior to the point where the meat becomes unsuitable for consumption.