The ability to rapidly detect biologically and environmentally significant metal ions such as zinc and mercury is important to study a number of important cellular and environmental processes. Hydrophilic bis(1,2,3-triazolyl)fluorene-based derivatives containing a 1,2,3-triazole-based recognition moiety were synthesized through Click chemistry and characterized by UV-vis absorption, fluorescence emission, and two-photon absorption as new fluorescence sensing probes, selective for Zn~(2+) and Hg~(2+) ions. The UV-vis absorption and fluorescence emission spectra of the complexes exhibited blue-shifted absorption and emission spectra upon chelation to Zn~(2+) and Hg~(2+) ions, resulting in ca. 2-fold enhancement in fluorescence. Fluorometric titration revealed that 1:2 and 1:3 ligand to metal complexes formed with binding constants of 10~8 and 10~(16) for Zn~(2+) and Hg~(2+), respectively. The two-photon absorption cross sections for the probes and probe-metal ion complexes ranged from 200 to 350 GM at 800 nm. These novel fluorescent compounds may have potential as new metal ion sensors to probe cellular and biological environments.
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