A novel chemosensor, namely 3-(4-chlorophenyl)-1-(pyridin-2-yl)prop-2-en-1one, CPPEO, and its metal complexes have been synthesized and characterized by using sets of chemical and spectroscopic techniques, such as elemental analysis, mass, Fourier transform-infrared and UV-Vis spectral analysis. The thermal properties of the metal complexes have been investigated by thermogravimetric techniques. The decomposition mechanism of the titled complexes was suggested. The results showed that the Co 2+ and Mn 2+ complexes have an octahedral geometry, while Zn 2+ and Cd 2+ complexes have tetrahedral geometry. The kinetic and thermodynamic parameters of the thermal decomposition stages have been evaluated using the Coats-Redfern method. The optical sensing response of the investigated chemosensor to the different metal ions was investigated. It responds well to the tested metal ions as reflected from the significant change in both absorption and emission spectra upon adding different concentrations of the metal salts, confirming the intramolecular charge transfer of the chemosensor upon effective coordination with the used metal ions.This leads to enhancing ICT interaction, causing a significant shift in the presence of strongly complexing metal ions. This was fully reversible, where the solution of dye-metal ion complex was decomplexed by adding an EDTA solution to revert the original spectrum of the dye. The stability constants, K, for the complexes of the investigated chemosensor with the mentioned metal ions were calculated, indicating that Co 2+ is the most effectively detected, and the potential of the novel dye was highly efficient switchers for Co 2+ ions. Additionally, the molecular modeling was carried out for the chemosensor and its metal complexes. Finally, the solid complexes have been tested for their in vitro antimicrobial activities against some bacterial strains (Gram +ve and Gram −ve bacteria), as well as antifungal strains.

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