Ferrocene/phenylboronic acid-bearing benzoic acids were prepared to study their electrochemical redox properties in the presence of D-fructose and D-glucose. 4-[
N-(2-boronobenzyl)-
N-(ferrocenylmethyl)aminomethyl] -benzoic acid (
1) exhibited reversible redox response originating from the ferrocene moiety in aqueous solutions containing methanol at pH 7.0, 8.0 and 9.0. The oxidation current of
1 in differential pulse voltammetry (DPV) decreased in the presence of D-fructose and D-glucose, depending on the concentration, owing to the binding of the sugars to phenylboronic acid moiety in
1. The decreased oxidation current may be ascribable to changes in the intra-molecular interaction between the boron and nitrogen atoms in
1. The response of
1 to D-fructose was higher than that to D-glucose because of the higher affinity of D-fructose. The changes in the oxidation current in DPV were observed in the concentration ranges of 1 × 10
−3 mol L
−1—5 × 10
−3 mol L
−1 or 1 × 10
−3 mol L
−1—1 × 10
−2 mol L
−1 for D-fructose and 1 × 10
−3 mol L
−1—2 × 10
−2 mol L
−1 mM for D-glucose. In contrast, 4-[
N-(3-boronobenzyl)-
N-(ferrocenylmethyl)aminomethyl] benzoic acid (
2) showed a negligible response to the sugars, probably due to a lack of intra-molecular interactions between boron atom and nitrogen atom in
2. It may be possible to immobilize
1 on the surface of electrodes because
1 contains the carboxylic acid moiety. Thus, a potential use of
1 in the construction of glucose sensors is suggested.
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