Boronic Acid-Based Bipyridinium Salts as Tunable Receptors for Monosaccharides and α-Hydroxycarboxylates

Abstract

Several novel diboronic acid-substituted bipyridinium salts were prepared and, using a fluorescent reporter dye, were tested for their ability to selectively bind various monosaccharides and alpha-hydroxycarboxylates in an aqueous medium. The fluorescence sensing mechanism relies on the formation of a ground-state charge-transfer complex between the dye and bipyridinium. An X-ray crystal structure of this complex is described herein. Glucose selectivity over fructose and galactose was achieved by designing the bipyridinium-based receptors to be capable of attaining a 1:1 receptor/substrate stoichiometry via cooperative diboronic acid binding.

Highly Efficient Suzuki–Miyaura Coupling of Heterocyclic Substrates through Rational Reaction Design

“…Even with the sterically hindered 1-naphthylboronic acid, quantitative conversion was achieved in the presence of 0.01 mol % of Pd catalyst (Table 3, entries [13][14][15][16][17][18][19]. Difficult substrates such as the highly basic 4-amino-2-chloropyridine reacted with p-tolyl- boronic acid or 1-naphthylboronic acid to afford quantitative conversions at 0.01 mol % catalyst loading (Table 3, entries 8, 16).…”

Expanding Roles for Organoboron Compounds – Versatile and Valuable Molecules for Synthetic, Biological and Medicinal Chemistry

“…Given the importance of glucose monitoring for patients with diabetes and for other applications, a great amount of effort has been directed towards the development of boronic acid-containing sensors that can operate under physiological conditions for routine monitoring. [56,57] Alternative applications of these boronic acid glucose sensors involve glucose imaging, and the use of novel polymeric materials that can be used for the controlled release of insulin on binding of glucose. [37] Finally, fluorescent boronic acid sensors can be used in a diagnostic manner for the detection and labelling of fucosylated oligosaccharides that occur in surface carbohydrates that are common in certain cancers.…”

Crystal Structure of 1,1′-dimethyl-[4,4′-bipyridine]-1,1′-diium tetrachloridozincate(II), C12H14Cl4N2Zn

“…Organically templated inorganic hybrid materials have attracted much interest due to their intriguing architectures and topologies as well as fascinating physical properties [3][4][5][6]. Viologen and related derivatives have been widely used as templates to construct metal-halide-viologen complexes with various structure types because of their application in biology, electrochemistry and photochemistry [7][8][9][10].…”