Synthesis, Characterization, and Computational Analysis of (E)-2-(2-(11HIndeno[1,2-b]quinoxalin-11-ylidene)hydrazineyl)-5-phenyloxazole Derivatives for Potential Electronic Applications

Introduction: This study aims to synthesize and characterize a novel series of (E)-2-(2- (11H-indeno[1,2-b]quinoxalin-11-ylidene)hydrazineyl)-5-phenyloxazole derivatives (7a–r) for potential application in organic and optoelectronic devices. The molecular design incorporates indenoquinoxaline and oxazole moieties, both recognized for their favorable electronic properties. Methods: The target compounds were synthesized via a multi-step procedure beginning with the condensation of 1H-indene-1,2,3-trione and benzene-1,2-diamine, followed by coupling with hydrazinecarboxamide and final reaction with 2-bromo-1-phenylethan-1-one derivatives. The reactions were optimized with respect to solvent choice and reaction time. Structural and electronic properties were analysed using density functional theory (DFT) at the RB3LYP/3-21G level. Results: Ethanol was identified as the optimal solvent, affording product yields up to 84% within 5 hours. DFT calculations confirmed structural stability across the series, with notable differences in electronic properties. Compound 7a showed high stability (ΔEgap = 3.44 eV), whereas 7j exhibited a narrow band gap (1.63 eV), indicating potential for enhanced charge transfer. Compound 7n displayed the highest dipole moment (7.82 Debye), suggesting suitability for polarity-sensitive applications. discussion: The synthesis of the derivatives was successful, with promising electronic properties identified through computational analysis. Compounds like 7a demonstrate stability, while 7j’s narrow energy gap suggests potential for better charge transport in optoelectronic devices. The high dipole moment in 7n indicates suitability for polarity-driven applications. These derivatives could be tailored for specific electronic functions, though further studies on their photophysical properties are needed. Discussion: The synthesized derivatives display a promising range of electronic properties that can be tailored for specific device functionalities. Computational analyses further support their potential for applications in organic electronics, particularly in contexts requiring molecular stability and tunable electronic band gaps. Conclusion: This study successfully demonstrates the synthesis and theoretical evaluation of a new class of heterocyclic compounds with potential applications in electronic and optoelectronic materials. Further photophysical investigations are recommended to validate their practical performance.