A BODIPY-based fluorescent chemosensor with 2, 6-substitution for visual and highly selective detection of S2–

BODIPY derivatives have often been employed as fluorescent sensors to probe toxic ions in environment and living systems, such as sulfide ion (S2-). Whilst many structure modifications have been exploited on groups at the 3, 5, 8-positions, there are quite few examples on tailoring the 2,6-substituents for chemosensor investigations. Herein, we design and synthesize a 2,6-substituted BODIPY molecule, LM-BDP, to use as a fluorescent probe for detecting S2- in aqueous media. The electronic and crystal structures of the probe are studied by density functional theory (DFT) calculations and single-crystal X-ray diffraction analysis. Spectroscopy investigations are performed in a variety of conditions, showing that LM-BDP exhibits a noticeable color change from pink to dark red and a fluorescence shift from yellow to pink channel with decreased intensity upon addition of S2-. The selectivity and sensitivity measurements show that LM-BDP can only response to S2- with a detection limit of 0.29 μM in less than 100 s. The remarkable contrast in fluorescence images in test-stripe and RAW 264.7 cell experiments indicates that the probe is a proper candidate for the application in detecting exogenous S2-.