A new colorimetric and fluorescent chemosensor for fluoride anion based on calix [4]arene bearing four sulfonamide-fluorenone subunits on the upper rim was conveniently synthesized. It showed a remarkable color change as well as the fluorescence quenching upon addition of F− even in the presence of a wide range of anions in DMSO. The binding property of L with F− was studied by a combination of various spectroscopic techniques, such as absorption and emission titration, Job's plot and 1 H NMR titration. It is anticipated that this design with functional group attached to upper rim of calix[4]arene platform can provide a new approach for the development of F− chemosensor.