Comparison of Absorption-Emission Properties of New Azo Dyes and New Schiff Bases from Benzimidazole Derivative 1,3,4-Thiadiazole and Theoretical Calculation by DFT Method

Abstract

After the synthesis of the new benzimidazole derivative 1,3,4-thiadiazole compound, a series of azo dyes from the reaction of this compound with various coupling components and a series of schiff bases were synthesized from the reaction with various aldehydes. The structures of the obtained compounds are characterized and interpreted with UV, FT-IR and 1H-NMR. The fluorescence properties of the compounds were also investigated, and the absorption and emission properties of schiff base and azo dyes obtained from the same derivative were examined. As a result, it was observed that schiff bases obtained from benzimidazole derivative 1,3,4-thiadiazole compound had longer wavelength absorption-emission compared to azo dyes obtained from the same compound. Experimental data were supported by density functional theory (DFT) calculations. The ground state geometries, spectroscopic properties, FMO energies and related chemical reactivity parameters of the compounds were calculated using the B3LYP hybrid density functional combined with 6-311++G(2d,2p) basis set. At the same theory level, QTAIM and IRI analyzes were also performed and the data were used to determine the properties of tautomeric structures. The electronic properties of the compounds were studied and a detailed analysis was performed by comparing them with experimental data.

Keywords

• Benzimidazole
• Azo dyes
• Schiff bases
• Fluorescence
• Absorption properties
• DFT method

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