Ferrocenyl-isoxazole derivative: a novel electrochemical, colorimetric and fluorescent multiple signal probe for highly selective recognition of Cu²⁺ ions

Abstract

In this paper, a novel compound 3-(2-quinolyl)-5-ferrocenyl-isoxazole(5) with high selectivity toward Cu2+ over other heavy and transition-metal(HTM) ions was designed and synthesized in good yields. The compound not only could be used as an electrochemical probe for Cu²⁺ with an anodic peak shift of Fe(II)/Fe(III) redox couple, but also could be a colorimetric and fluorescent probe due to the detectable change in color by naked eyes and a significant fluorescence quenching of monomeric anthracene moiety. This highly selective sensing of Cu²⁺ may be attributed to the unprecedented intermolecular electron-transfer reorganization after the oxidation of the first single electron of compound 5, as indicated by electrospray ionization mass spectrometry(ESI-MS) and density functional theory(DFT) calculation results. To the best of our knowledge, this class of compounds have rarely been reported in the field of molecular sensing. It may have a potential significance for the application of the ferrocenyl-isoxazole derivative in molecular recognition.

Keywords

Ferrocene / Isoxazole / Receptor / Recognition / Cu²⁺

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