Journal of the American Chemical Society, Vol.137, No.49, 15402-15405, 2015
Fluorinated Boronic Acid-Appended Bipyridinium Salts for Diol Recognition and Discrimination via F-19 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 F-19 NMR spectroscopy. An array of three water-soluble boronic acid receptors in combination with F-19 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 NMR fingerprints are interpreted as two-dimensional barcodes without the need of multivariate analysis techniques.