Fluorescence Sensing of Zinc and Mercury Ions with Hydrophilic 1,2,3-Triazolyl Fluorene Probes.

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. two-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 200-350 GM at 800 nm. These novel fluorescent compounds may have potential as new metal ion sensors to probe cellular and biological environments.