A method of preparation of new representatives of donor-acceptor stilbazoles based on pyridine-2-thione containing a cyano group and a trifluoromethyl moiety in the acceptor part of the molecule was developed. The synthesized stilbazoles exhibited pronounced fluorescence, with quantum yields up to about 15 % significantly improved compared to traditional thioxonicotinonitriles, which typically lack such properties. The emission turned out to be strongly dependent on the tautomeric equlibrium in the solution that was studied using both computational methods and comprehensive spectroscopic analysis. Solvato(fluoro)chromism and the influence of the substituent on the spectral characteristics of the compounds were also investigated. It was established that the emission maximum could be tuned from 418 to 630 nm covering almost the entire visible spectrum. The design of stilbazoles enhanced their photophysical properties making them suitable candidates for environmental monitoring or biological sensing. As a result a new chemosensor was developed demonstrating high selectivity for the detection of micromolar concentration of mercury(II) ions (LoD 1.34 μM) and submicromolar concentration of cadmium(II) ions (LoD 0.875 μM) in aqueous media.
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