Rational design of fluorescent probe for Hg2+ by changing the chemical bond type

Abstract

Two kinds of fluorescent probes DFBT and DFABT, and their corresponding water-soluble compounds WDFBT and WDFABT, based on the trimers containing a benzo[2,1,3]thiadiazole moiety and two fluorene moieties are synthesized. Their luminescent behavior towards Hg²⁺ ions and other various metal ions in organic and water solutions are studied in detail via absorption and emission spectroscopy. All these probes show a selective “on–off-type” fluorescent response to Hg²⁺ ions in solution over other metal ions with a maximum detection limit of 10⁻⁷ M. Importantly, the probe type can be changed from irreversible to reversible by altering the bridge mode between the functional units from CC triple bond to C–C single bond. Their detection mechanisms towards Hg²⁺ are studied in detail via mass spectrometry and Job plots, which are attributed to irreversible chemical reaction for DFABT and WDFABT and a reversible coordination reaction for DFBT and WDFBT respectively. Our research results about this kind of organic fluorescent probe provide valuable information to the future design of practical Hg²⁺ fluorescent probes.