Tuning the sensitivity towards mercury via cooperative binding to d-fructose: dual fluorescent chemosensor based on 1,8-naphthyridine-boronic acid derivative

Abstract

A novel fluorescent chemosensor naphthyridine-boronic acid derivative (1.1) was synthesized and its ability to act as a selective chemosensor was examined for various metal ions. Compound 1.1 displayed highly selective fluorescence quenching upon interaction with Hg²⁺, possibly by means of photo induced electron transfer (PET) mechanism. The binding stoichiometry of the naphthyridine-boronic acid–Hg²⁺ complex and the association constant was determined. It was found that in the presence of D-fructose at physiological concentration, the sensitivity of chemosensor 1.1 towards Hg²⁺ improved by at least 7 times, perhaps as a result of the cooperative binding of both D-fructose and mercury ion to the sensor. Till now, the presented dual D-fructose–mercury chemosensor is the first example of utilizing boronic acid–diol complexation for enhancement of the sensor's sensitivity towards a toxic metal ion. The utility of compound 1.1 lays in applications in the food industry, e.g. for detection of mercury contamination of high fructose corn syrup, or in estimation of mercury in polluted biological samples and underground water.