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Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
Published on: August 19, 2013
A halogen bonding BODIPY-appended aza-crown ether for selective optical sensing of inorganic and organic ion-pair
Jamie T Wilmore1, Andrew J Taylor1, Igor Marques2
1Department of Chemistry, Chemistry Research Laboratory, University of Oxford Mansfield Road Oxford OX1 3TA UK paul.beer@chem.ox.ac.uk.
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.
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