A novel series of chiral Schiff base ligands S1, S2, S3, S4, A1 and A2 was successfully designed and synthesized via the condensation of orthophthalaldehyde (OPA) with various chiral 1,2-diamines, amino acids, and ortho-aminobenzaldehyde under optimized reaction conditions. These ligands were engineered to function as multi-dentate donor frameworks, explicitly separating into N4 tetradentate systems S1, S2, S3, S4 and N2O2 tetradentate systems A1, A2. The corresponding coordination complexes were subsequently synthesized by reacting these newly prepared ligands with divalent transition metal ions, specifically Manganese (II), and Palladium (II). Complete structural and physical characterization of both the free ligands and their metal complexes was systematically accomplished utilizing elemental (CHN) analysis, mass spectrometry, Fourier-transform infrared (FT-IR) spectroscopy, multinuclear NMR 1H and 13C spectroscopy, electronic absorption spectroscopy, molar conductance measurements, magnetic susceptibility, electron spin resonance (ESR), and thermogravimetric analysis (TG-DTA). The experimental values obtained across all analytical techniques showed exceptional agreement with the proposed molecular formulas and tentative coordination structures. Molar conductance data revealed that the A1 and A2 coordination complexes exist as non-electrolytes across all metal systems due to internal charge neutralization via deprotonated phenolic or carboxylic groups. Conversely, the S1, S2, S3, and S4 complexes display non-electrolytic properties in Mn (II) frameworks where chlorides coordinate within the inner sphere, but transition into 1:2 electrolytic variants with Pd (II) matrices. Electronic absorption spectra combined with magnetic moment values validated high-spin octahedral environments for all Mn (II) systems, square planar geometries for the S-series Pd (II) systems. Thermal decomposition profiles substantiated the presence of coordinated and lattice water molecules uniquely within the A1 and A2 complexes, while indicating high thermal stability for the anhydrous S-series systems.