Terpyridines are well-known ligands in coordination chemistry, are valued for their conformational flexibility and strong metal-binding properties, and are also of interest as fluorophores. This study focused on the synthesis and comprehensive investigation of a new class of bis-oxazolo[5,4-b]pyridine derivatives, designed based on
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Terpyridines are well-known ligands in coordination chemistry, are valued for their conformational flexibility and strong metal-binding properties, and are also of interest as fluorophores. This study focused on the synthesis and comprehensive investigation of a new class of bis-oxazolo[5,4-b]pyridine derivatives, designed based on their structural similarity to terpyridines. Four novel compounds,
4a–
d, were synthesized by cyclization of amide derivatives of 3-aminopyridin-2(1
H)-ones using pyridine-2,6-dicarboxylic acid and its dichloride as key acidic components. Their structures and purity were confirmed by melting point analysis, high-resolution mass spectrometry, and
1H,
13C NMR spectroscopy. Compounds
4a–
c exhibit UV absorption at 323–357 nm and intense blue to deep-blue fluorescence (357–474 nm, цi ≈ 0.32–0.84) in chloroform, dichloromethane, and acetonitrile, attributed to p–p* transitions within the conjugated ring system. These findings suggest their potential as phosphors for organic electronics. Computational modeling of
4a–
c molecules provided insight into their electronic structures, conformational stability, and predicted optical behavior. The most stable conformers (
4a–
II,
4b–
II,
4c–
II′) exhibited a progressive decrease in the HOMO–LUMO gap from
4a to
4c, correlated with the enhancement of photoactivity. Among them, compound
4a stands out as the most promising luminophore, displaying the most intense and narrow luminescence band, owing to its high molecular symmetry and stable emission characteristics. Overall, this study lays the foundation for future studies of bis(oxazolo[5,4-b]pyridine) derivatives in coordination chemistry and optoelectronic materials development.
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