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 that the receptor exhibits significant selectivity for the 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.
keywords
BINDING; COOPERATIVITY; RECOGNITION; FERROCENE; RECEPTOR
subject category
Chemistry
authors
Wilmore, JT; Taylor, AJ; Marques, I; Felix, V; Beer, PD
our authors
Igor Oliveira Marques
Junior Researcher
Vítor Félix
Associate Professor with AggregationProjects
CICECO - Aveiro Institute of Materials (UIDB/50011/2020)
CICECO - Aveiro Institute of Materials (UIDP/50011/2020)
Associated Laboratory CICECO-Aveiro Institute of Materials (LA/P/0006/2020)
acknowledgements
J. T. W. thanks the EPSRC for a Doctoral Prize (EP/W524311/1). A. J. T. thanks the EPSRC for a studentship (EP/T517811/1). The theoretical studies were developed within the scope of the project CICECO-Aveiro Institute of Materials, UIDB/50011/2020 (DOI 10.54499/UIDB/50011/2020), UIDP/50011/2020 (DOI 10.54499/UIDP/50011/2020) & LA/P/0006/2020 (DOI 10.54499/LA/P/0006/2020), financed by national funds through the FCT/MCTES (PIDDAC).