Design, synthesis and structure of new potential electrochemically active boronic acid-based glucose sensorsThis work was supported by the Danish National Technical Research Council (grant 9900690).

Abstract

In the course of our investigations on new boronic acid based carbohydrate sensors three new boronic acids 3, 7 and 11 containing a ferrocene moiety were synthesised. Their design includes an intramolecular B–N bonding motif in order to facilitate binding at physiological pH. We report the synthesis of the compounds and our investigations on glucose complexation as studied by ¹³C NMR spectroscopy. The crystal structure of 2,4,6-tris[2-(N-ferrocenylmethyl-N-methylaminomethyl)phenyl]boroxin (13) (boroxin of boronic acid 3) (boroxin = cyclotriboroxane) was obtained and compared with structures obtained of 2,4,6-tris[2-(N,N-dimethylaminomethyl)phenyl]boroxin (14) and 2,2-dimethyl-1,3-diyl[2-(N,N-dimethylaminomethyl)phenyl]boronate (15). The structure of 13 shows the existence of intramolecular B–N bonds in the solid phase.