The design, synthesis, characterization and their anion sensing properties of two receptors capable of exhibiting azo-hydrazone tautomerism are reported. The anion sensing properties have been investigated using electronic, fluorescence and nuclear magnetic spectral studies in addition to electrochemical and visual detection experiments. Both the receptors selectively bind fluoride ion with >100 nm red-shift in the electronic spectrum and the color changes from yellow to red. The results of the spectral studies revealed that the sensing mechanism involves fluoride ion induced change of chromophore from Cdouble bond; length as m-dashN (hydrazone form) to Ndouble bond; length as m-dashN (azo form) in these receptors leading to the visible color change. Density Functional Theory calculations were conducted to rationalize the optical response of the receptors.