Fluoroalkoxy-Functionalized Pyrazolines as Dual-Purpose Candidates for Optoelectronic and Pharmaceutical Applications: A Combined Experimental–Theoretical Study

https://doi.org/10.5281/zenodo.19414275

Abstract

Fluoroalkoxy-functionalized pyrazoline derivatives were synthesized and systematically evaluated as dual-purpose molecular candidates for optoelectronic and pharmaceutical applications through a combined experimental–theoretical approach. Structural confirmation was achieved via spectroscopic techniques, while density functional theory (DFT) and time-dependent DFT (TD-DFT) calculations were employed to investigate electronic structure, charge distribution, and optical behavior at the B3LYP/3-21G level of theory. Optimized geometries revealed a donor–acceptor architecture resulting from electron-withdrawing fluorine and electron-donating alkoxy substituents, promoting intramolecular charge transfer across the pyrazoline core. Frontier molecular orbital analysis indicated spatial separation of HOMO and LUMO, with the methoxy-substituted derivative exhibiting the smallest energy gap and highest softness among the series. TD-DFT results predicted absorption in the UV–visible region with allowed π→π* transitions and measurable oscillator strengths, highlighting optoelectronic responsiveness. Molecular electrostatic potential mapping identified distinct electron-rich heteroatoms and electron-deficient regions, supporting potential interaction with biological targets. In silico ADMET prediction confirmed compliance with Lipinski’s rule of five and favorable pharmacokinetic profiles. The methoxy derivative demonstrated the most balanced combination of reduced energy gap, enhanced charge transfer, and acceptable drug-likeness parameters. The study establishes a clear structure–property–application relationship and demonstrates that fluoroalkoxy substitution effectively tunes pyrazoline derivatives toward multifunctional performance in both optoelectronic and pharmaceutical domains