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...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-12, Vol.137 (49), p.15402-15405
Main Authors: Axthelm, Jörg, Görls, Helmar, Schubert, Ulrich S, Schiller, Alexander
Format: Article
Language:English
Online Access:Get full text
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b10934