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We report a set of novel receptors with the structural feature of having an naphthyl-, pyrenylor ferrocenyl subunits, directly linked to a 2-aza-1,3-butadiene moiety which, in general, can be used for the rapid and selective detection of Hg. After coordination with this metal cation, the derivatives having two different signaling units, such as a fluorophore and a redox moiety, undergo significant changes not only in their oxidation potentials but also in their UV-vis and emission spectra. Interestingly, in such cases addition of Cu cation promotes the oxidation of the free ligands. By contrast, pyrenyl derivative 10 selectively senses both Hg and Cu through two different channels: colorimetric and fluorescent. Furthermore, the association constants for the 1:1 complexes formed as well as the detection limits for the analysis of Hg and Cu are also reported. These findings are not only a supplement to the detecting methods for these pollutant metal ions, but also adds new merits to the chemistry of the 2-aza-1,3-butadiene derivatives.

2-Aza-1,3-butadiene ligands for the selective detection of Hg2+ and Cu2+ ions