A Halogen Bonding BODIPY-appended Aza-Crown Ether for Selective Optical Sensing of Inorganic and Organic Ion-Pair Species

Abstract

A novel ion-pair receptor, consisting of a diaza-18-crown-6 cation binding motif and a BODIPY-appended halogen bonding optical anion-sensing motif, is prepared and shown to be a potent receptor for inorganic and organic ion-pairs. Comprehensive optical emission and ¹H NMR spectroscopic titration studies, in combination with computational investigations, demonstrate the receptor exhibits significant selectivity for ion-pair guest species K⁺/Cl⁻ over other alkali metal halide ion-pairs and the neurotransmitter salt dopamine hydrochloride over other phenethylamine hydrochloride derivatives. Notably, the specific host-guest three-dimensional binding mode, resulting from the simultaneous participation of the heteroditopic receptor’s multiple proximal convergent binding motifs, dictates the observed inorganic and organic ion-pair selectivity trends, representing a potent biomimetic strategy for the design of optical sensors for a range of biologically-relevant ion-pair analytes.