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This study employs DFT and TD\u2010DFT based calculations to investigate fluorinated low\u2010bandgap \u03c0\u2010conjugated systems featuring a benzodifurandione core linked to oxindole units, with chalcogen variation (O, S, Se) in the central framework. Electronic structure analysis reveals a progressive redshift in absorption and photoluminescence spectra from O to Se, attributed to enhanced \u03c0\u2010conjugation and increased atomic polarizability, reducing the HOMO\u2010LUMO gap. M3 (X\u2009=\u2009Se) demonstrates the most redshifted optical properties, making it ideal for near\u2010infrared (NIR) applications. Bulk heterojunction (BHJ) device assessments yield power conversion efficiencies (PCEs) of up to 7.00%, highlighting their potential in high\u2010performance OSCs. Non\u2010covalent interactions (NCIs), including hydrogen bonding and van der Waals forces, are characterized using Hirshfeld surface analysis, reduced density gradient (RDG) scatter plots, and the quantum theory of atoms in molecules (QTAIM), emphasizing their influence on molecular packing and stability. Electron localization function (ELF) and localized orbital locator (LOL) analyses further elucidate the balance of covalent and non\u2010covalent interactions governing optoelectronic behavior. 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