The fluorescent sensor 3 based on the 1,3-alternate conformation of thiacalix[4]arene bearing the coumarin fluorophore via an imino group has been synthesized. The sensing properties were evaluated in terms of a colorimetric and fluorescence sensor for Zn 2+ and F -. High selectivity and excellent sensitivity were exihibited, and "off-on" optical behavior in different media was observed. Changes were all visible to the naked eye, whilst the presence of the Zn 2+ and Finduces fluorescence enhancement and the formation of a 1:1 complex with sensor 3. In addition, the sensor 3 has low cytotoxicity and good cell permeability, and can readily be employed for assessing the change of intracellular Zn 2+ and Flevels.