Charge transfer complexes developed during the interaction of Fluconazole drug (FLU) as an electron donor with different types of electron acceptors, including σ-type as iodine (I2), and π-types as 2,3-dinitrosalsylic acid (HDNS), Tetracyanoethylene (TCNE) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The formed complexes were characterized using various techniques as UV–Vis spectra, Thermal analyses, spectrophotometric measurements, 1H NMR and FTIR Spectroscopy. It was found that the stoichiometry of all developed complexes was a 1:1 M ratio between fluconazole and acceptors (I2, HDNS, TCNE and DDQ). The characteristic physical parameters data such as ionization potential (ID), The oscillator strength (ƒ), formation constant (KCT), transition dipole moment (μ), free energy (ΔG), and energy of interaction (ECT) of the formed CT-complexes have also been reported. Eventually, the synthesized complexes were screened for their microbial and antioxidant activities.