Structure–Property Relationship in π‑Conjugated Bipyridine Derivatives: Effect of Acceptor and Donor Moieties on Molecular Behavior

Here, we reported the photophysical studies, single-crystal X-ray crystallography, and density functional theory (DFT) calculations of two bipyridine derivative molecules. In addition, thermal gravimetric analysis and cyclic voltammetry studies were also performed for both compounds. According to crystallographic data, the π-conjugated molecules have high-quality crystal structures as a result of intramolecular and intermolecular hydrogen bonds occurring through the molecules of the compound. It was determined that when the functional groups (F– and CH3O−) were introduced to the para positions, the molecules adopted slipped stacking (J-aggregate) and antiparallel cofacial stacking (H-aggregate). It was observed that these two bipyridine derivatives disclose the relationship between molecular conformation-molecular packing modes and photophysical behavior of organic solids. The results of DFT calculations supported the structural, spectroscopic, and photophysical data and confirmed the compositions of frontier molecular orbitals in both molecules.