Water-soluble deep cavitands with cationic functions at the lower rim can selectively bind iodide anions in purely aqueous solution. By pairing this lower rim recognition with an indicator dye that is bound in the host cavity, optical sensing of anions is possible. The selectivity for iodide is high enough that micromolar concentrations of iodide can be detected in the presence of molar chloride. Iodide binding at the “remote” lower rim causes a conformational change in the host, displacing the bound dye from the cavity and effecting a fluorescence response. The sensing is sensitive, selective, and works in complex environments, so will be important for optical anion detection in biorelevant media.
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An arrayed combination of water-soluble deep cavitands and cationic dyes has been shown to optically sense insect pheromones at micromolar concentration in water. Machine learning approaches were used to optimize the most effective array components, which allows differentiation between small structural differences in targets, including between different diastereomers, even though the pheromones have no innate chromophore. When combined with chiral additives, enantiodiscrimination is possible, dependent on the size and shape of the pheromone.more » « less
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A water-soluble host molecule can bind tetrahydrocannabinol ( Δ9-THC ) and its metabolites in aqueous solution. By pairing this recognition event in a sensing array with fluorescent reporters and varying external mediators, pattern recognition-based detection is possible, which allows selective discrimination of the THC metabolites. The selective sensing can be performed in aqueous solution with micromolar sensitivity, as well as in biofluids such as urine and saliva. Metabolites as similar as Δ8- and Δ9-THC , differing only in the position of a double bond, can be distinguished.more » « less
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Arrayed cavitand:fluorophore sensor complexes can selectively sense small citrulline modifications at arginine residues on post-translationally modified peptides. The sensor can differentiate between different numbers of citrulline modifications, and a simple two-fluorophore, 6-component array can effect cross-reactive discrimination between single modifications in aqueous solution.more » « less
