Synthesis of novel bi-Zwitterion Schiff base derivate from 4‑hydroxy-2H-pyran-2-one: DFT/HSA-interactions, thermal, physicochemical, TD-DFT and optical activity

A novel tetradentate bi-Zwitterion Schiff base (SB): 3,3′-((1E,1′E)((oxybis(4,1-phenylene))-bis-(azanylylidene))-bis(ethan-1-yl-1-ylidene))bis(4‑hydroxy-2H-pyran-2-one) was synthesized, via reflux condensation of 3-acetyl-4‑hydroxy-6-methyl-2H-pyran-2-one with 4,4′-oxydianiline in methanol. The SB ligand was characterized using various physicochemical techniques, including 1HNMR , elemental analysis (CHN-EA), XRD, MS, UV–vis, and FT-IR. The XRD analysis confirmed the presence of a bi-zwitterionic salt form, characterized by intra-H-bond interactions between [N+—H…−O] groups. Hirschfield surface analysis (HSA) and MEP/MAC/NPA were conducted to gain insight into the intra/intermolecular hydrogen bond interactions of the molecule. The completion of the SB dehydration reaction was UV–vis., tracked by studying the behavior of the reactants before and after mixing. Additionally, the absorbance/transmittance, TD-DFT, and optical properties of the SB were evaluated. Finally, the TG/DTG analysis was used to determine the thermal stability of the desired SB ligand.