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  • Title: Organochalcogen substituted dimesityl borane-imidazoles as fluorogenic fluoride and cyanide sensors in aqueous media.
    Author: Parveen S, Naaz F, Prasad DLVK, Anantharaman G.
    Journal: Analyst; 2023 May 16; 148(10):2362-2374. PubMed ID: 37128863.
    Abstract:
    Natural and anthropogenic activities leading to excessive toxic biological anions in water have warranted the development of anion sensors, especially for cyanide (CN-) and fluoride (F-) ions in aqueous media. Herein, a contemporary synthetic route to embed organochalcogen compounds (-SPh and -SePh) in a boron-functionalized imidazole scaffold via metal halogen exchange is reported. Upon methylation, fluorogenic compounds 5-dimesitylboryl-2-phenylthio-1-methylimidazole (7) and 5-dimesitylboryl-2-phenylselone-1-methylimidazole (8) form the corresponding imidazolium salts, 5-dimesitylboryl-2-phenylthio-1-methylimidazolium iodide (9) and 5-dimesitylboryl-2-phenylselone-1-methylimidazolium iodide (10), which are non-luminescent. All of the compounds are thoroughly characterized, and their utility in sensing F-, CN-, and various other biologically relevant halides has been studied through UV-vis and fluorescence spectroscopy. The substrates and products of 1 : 1 binding of anions (F-/CN-) with the compounds have been established by spectroscopy, spectrometry, single-crystal X-ray crystallography, and first principles quantum mechanical theoretical calculations. The superior binding ability and micromolar sensitivity towards CN- ions over other anions in aqueous media were elucidated. The reversibility of compound 7 was also tested and it was found that fluoride binding was reversible while cyanide binding was not.
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