A series of new aryl-substituted pyrazolone derivatives 5(a-h) were synthesised via the Baylis-Hillman acetate reaction with pyrazolones and tested for antifungal, antibacterial, and antioxidant properties in vitro. Among the tested molecules 5d and 5e show good in vitro antifungal and antibacterial activities due to the presence of fluorine, which enhances the absorption rate by increasing lipid solubility and improves the pharmacological activity. It is also evident from the results obtained from structure-activity relationship (SAR) studies. Further, the photophysical properties of synthesized compounds were theoretically estimated using the ab-intio technique. The ground state optimization and HOMO–LUMO energy levels are calculated using the DFT-B3LYP-6-311 basis set. Using the theoretically estimated HOMO–LUMO value, global chemical reactivity descriptor parameters are estimated, and the result shows that compounds 5d and 5e have a higher electronegative and electrophilicity index than other molecules. Overall results suggest that, fluorine substituted pyrazolone derivatives show good photophysical, SAR, and biological properties.