Organochalcogen substituted dimesityl borane-imidazoles as fluorogenic fluoride and cyanide sensors in aqueous media.
Sabeeha ParveenFarha NaazDasari L V K PrasadGanapathi AnantharamanPublished in: The Analyst (2023)
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.
Keyphrases
- ionic liquid
- high resolution
- quantum dots
- lymph node metastasis
- single molecule
- drinking water
- dna binding
- fluorescent probe
- solid state
- molecular dynamics
- energy transfer
- magnetic resonance imaging
- dna methylation
- aqueous solution
- molecular docking
- body mass index
- molecular dynamics simulations
- squamous cell carcinoma
- gene expression
- water soluble
- contrast enhanced
- monte carlo