2,2'-(1E,1'E)-2,2'-(1,10-phenanthroline-2,9-diyl)bis(ethene-2,1-diyl)bis(2,1-phenylene) diacetate (probe 1) was synthesized by condensation reaction in acetic anhydride from 2,9-dimethyl-1,10-phenanthroline and salicylic aldehyde, then hydrolyzed to yield 2,2'-(1E,1 'E)-2,2'-(1,10-phenanthroline-2,9-diyl)bis (ethene-2,1-diy1) diphenol (probe 2). The molecular structure of large conjugated were characterized by H-1 NMR, C-13 NMR, IR and MS. Excellent luminescent properties of probes 1 and 2 showed that different fluorescence quenching effect for Cu2+ and Ag+. Probe 2 with a dual-function ion recognition performance exhibited for F- and AcO- anions. The complexes composition, stability constants, thermodynamic parameters and complexation model were evaluated using spectral titration, isothermal titration calorimetry and mass spectrometry. The complexation of probes and metal ions with 2:1 molar ratio were exothermic reaction.