N-acyl triazenes as tunable and selective chemodosimeters toward cyanide ion

A novel type of chemodosimeters has been developed on the basis of a displacement reaction. N-Acyl-triazenes are found to be highly selective and tunable chemodosimeters toward cyanide. When N-acetyl-triazene 1a was titrated with various anions (-CN, F-, Cl-, AcO-, H2PO4-, -SCN, ClO4-, and HSO4-) in acetonitrile, significant absorption changes (from colorless to deep purple) resulted in the cases of -CN and F-, and small changes in the cases of AcO- and H2PO4-. N-Isopropanoyl-triazene 1b showed significant response only toward -CN, weaker response toward F-, and little response toward other anions in acetonitrile. Both of the triazenes 1a and 1b responded only to -CN in methanol-water, because of the analyte's strong nucleophilicity toward the acyl group and weak hydrogen-bonding ability as compared to other anions examined. The N-acyl-triazenes can be used for the naked eye detection of cyanide.