Effect of fluorine position on the structural, electronic, and docking properties of conjugated hydrazone and diazenium naphthalenone derivatives: experimental and computational insights

Two fluorinated π-conjugated systems were examined using DFT to clarify the effect of fluorine position. DFT results showed excellent agreement with experimental data. Hirshfeld surfaces and energy frameworks revealed that both structures are stabilized by dispersion forces and weak contacts. Vibrational assignments confirmed all characteristic modes. Topological analyses revealed noncovalent interactions. NBO indicated hyperconjugation and charge transfer, consistent with the lower FMOs gap (2.01 eV) compared to EFDNO (3.04 eV). MEP demonstrated that para-fluorine substitution promotes more symmetric charge distribution. Molecular docking showed strong affinities for several biological targets, particularly EFOND/2IID (–8.2 kcal·mol−1) and EFDNO/2IID (–9.0 kcal·mol−1). ADMET and toxicity predictions highlighted favorable drug-likeness for both molecules.