A straightforward design of receptors for binding and sensing of sulfate in aqueous medium was developed. The design involves the connection of two naphthalimide-based pH probes through a hydrogen-bonding motif. The structure of the receptor-sulfate complex, predicted by DFT calculations, was unambiguously confirmed by NMR measurements. There are three major interactions stabilizing the host-guest complex: electrostatic interactions, hydrogen bonding, and stacking interactions of the dyes. Study of two control receptors containing either one dye or methyl amide groups instead of amides, revealed that electrostatic and hydrogen bonding interactions contribute the most to affinity and selectivity of receptors. The receptors can detect sulfate in a 1:1 THF-buffer mixture in pH window 3.6-4.5 demonstrating up to 7-fold fluorescence enhancement. To the best of our knowledge, the reported PET (photoinduced electron transfer) anion probes possess the largest response for sulfate in aqueous solution yet described.
Keywords: anion recognition; fluorescence sensing; naphthalimide; selectivity; sulfate.
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