Synthesis, molecular structure, spectral investigation on (E)-1-(4-bromophenyl)-3-(4-(dimethylamino)phenyl)prop-2-en-1-one

In this work, an organic nonlinear optical material (E)-1-(4-bromophenyl)-3-(4-(dimethylamino)phenyl)prop-2-en-1-one (C17H16NOBr) was synthesized by reacting 4-bromoacetophenone and N,N-dimethyl benzaldehyde in ethanol in the presence of sodium hydroxide. FT-IR and FT-Raman spectra were recorded in the region 4000–500 cm−1 and 4000–50 cm−1, respectively. The structural and spectroscopic data of the molecule in the ground state were calculated by using density functional method (B3LYP) with 6-311++G(d,p) basis set. The vibrational frequencies were calculated and compared with the experimental frequencies, which yield good agreement between observed and calculated frequencies. The infrared and Raman spectra were also predicted from the calculated intensities. 1H NMR spectrum was recorded in CDCl3 and 1H NMR chemical shifts of the molecule were calculated using the gauge independent atomic orbital (GIAO) method. UV–visible spectrum of the compound was recorded in water in the range of 200–800 nm and the electronic properties were calculated by time-dependent density functional theory (TD-DFT) approach. Besides, Mulliken atomic charges, molecular electrostatic potential (MEP) were performed. Nonlinear optical features and thermodynamic properties were also outlined theoretically. The geometric parameters, energies, harmonic vibrational frequencies, chemical shifts and absorption wavelengths were compared with the available experimental data of the molecule. Comprehensive theoretical and experimental structural studies on the molecule were carried out by FT-IR, FT-Raman, NMR and UV spectrometry.