Fluorinated Boronic Acid-Appended Bipyridinium Salts for Diol Recognition and Discrimination via 19F NMR Barcodes

Fluorinated boronic acid-appended benzyl bipyridinium salts, derived from 4,4′-, 3,4′-, and 3,3′-bipyridines, were synthesized and used to detect and differentiate diol-containing analytes at physiological conditions via 19F NMR spectroscopy. An array of three water-soluble boronic acid receptors in combination with 19F NMR spectroscopy discriminates nine diol-containing bioanalytescatechol, dopamine, fructose, glucose, glucose-1-phosphate, glucose-6-phosphate, galactose, lactose, and sucroseat low mM concentrations. Characteristic 19F NMR fingerprints are interpreted as two-dimensional barcodes without the need of multivariate analysis techniques.