Synthesis and study of nonlinear optical properties of an enaminone derived from dibenzoylmethane and N,N-diethylaminoaniline

• Published in: Physica scripta 2024-10, Vol.99 (10), p.105915
• Main Authors: Elias, Rita S, Hassan, Qusay M A, Saeed, Bahjat A, Sultan, H A, Hansen, Poul Erik, Emshary, C A
• Format: Article
• Language: English
• Subjects: diffraction patterns; Nonlinear optical properties; Z-scan
• ISSN: 0031-8949; 1402-4896
• DOI: 10.1088/1402-4896/ad720c

The compound, (Z)-3-((4-(diethylamino)phenyl)amino)-1,3-diphenylprop-2-en-1-one, is synthesized by the reaction of dibenzoylmethane and 4-N,N-diethylaniline. The relative stabilities of the possible tautomers of the molecule are studied via the DFT B3LYP-D3BJ, CAM-B3LYP, M062X, and ωB97XD functionals in conjunction with the 6-311++G(d,p) basis set. The results showed that the enaminone tautomer with the intramolecularly hydrogen bonded chelated ring is the most stable. This is further confirmed by the Car–Parrinello MD calculations in the gas phase as well as the NCI analysis. The electronic spectrum is calculated by the TD DFT B3LYP/c-pVDZ level in ethanol, and the hole–electron analysis is carried out for the interpretation of the bands, which revealed that the longest one at 430 nm is of charge transfer origin while the others are of local transition origin. Atoms-in-molecules calculations in several media and levels of theory predicted that the ρ BCP at the hydrogen bond in the gas phase to be 0.03791–0.04255 e/a 0 3 which is a characteristic of a medium strong hydrogen bond. Researchers investigated the enaminone’s nonlinear optical (NLO) characteristics when it was exposed to a low power (