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

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Authors

LACINA Karel NOVOTNÝ Jan MORAVEC Zdeněk SKLÁDAL Petr

Year of publication 2015
Type Article in Periodical
Magazine / Source Electrochimica Acta
MU Faculty or unit

Central European Institute of Technology

Citation
Web http://www.sciencedirect.com/science/article/pii/S001346861402444X
Doi http://dx.doi.org/10.1016/j.electacta.2014.12.009
Field Electrochemistry
Keywords Ferroceneboronic acid; Lewis acid; Non-aqueous environment; Binding properties; Detection of saccharides
Description 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 non-aqueous 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 potential was 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 behaviour were confirmed by 1H and 11B NMR spectroscopies. The binding constants of the tested diols in aqueous and non-aqueous media were determined and compared.
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