Interaction of ferroceneboronic acid with diols at aqueous and non-aqueous conditions - signalling and binding abilities of an electrochemical probe for saccharides

摘要

Ferroceneboronic acid (FcBA) was employed as a model compound for clarification of binding and signalling properties of molecular probe for saccharides. As the simplest electrochemically active boronic acid, its interactions with diverse diols were studied in homogeneous phase under aqueous and nonaqueous conditions. The FcBA-diol system was examined by cyclic voltammetry resulting in two redox pairs corresponding to free and bound forms of FcBA. Redox potential of the bound form of FcBA was shifted in the cathodic direction in aqueous conditions due to coordination of the hydroxyl group to the boron atom. Oppositely, the anodic shift of the redox potentialwas observed upon the interaction of FcBA with diols in non-aqueous solvents. The binding properties and signalling mechanism of electrochemically active boronic acids were deduced and the assumptions resulting from the electrochemical behaviourwere confirmed by H-1 and B-11 NMR spectroscopies. The binding constants of the tested diols in aqueous and non-aqueous media were determined and compared. (C) 2014 Elsevier Ltd. All rights reserved.