FT-IR, UV–vis, 1H and 13C NMR spectra and the equilibrium structure of organic dye molecule disperse red 1 acrylate: A combined experimental and theoretical analysis

This study reports the characterization of disperse red 1 acrylate compound by spectral techniques and quantum chemical calculations. The spectroscopic properties were analyzed by FT-IR, UV–vis, 1H NMR and 13C NMR techniques. FT-IR spectrum in solid state was recorded in the region 4000–400 cm−1. The UV–vis absorption spectrum of the compound that dissolved in methanol was recorded in the range of 200–800 nm. The 1H and 13C NMR spectra were recorded in CDCl3 solution. The structural and spectroscopic data of the molecule in the ground state were calculated using density functional theory (DFT) employing B3LYP exchange correlation and the 6-311++G(d,p) basis set. The vibrational wavenumbers were calculated and scaled values were compared with experimental FT-IR spectrum. A satisfactory consistency between the experimental and theoretical spectra was obtained and it shows that the hybrid DFT method is very useful in predicting accurate vibrational structure, especially for high-frequency region. The complete assignments were performed on the basis of the experimental results and total energy distribution (TED) of the vibrational modes, calculated with scaled quantum mechanics (SQM) method. Isotropic chemical shifts were calculated using the gauge-invariant atomic orbital (GIAO) method. A study on the electronic properties were performed by timedependent DFT (TD-DFT) and CIS(D) approach. To investigate non linear optical properties, the electric dipole moment μ, polarizability α, anisotropy of polarizability Δα and molecular first hyperpolarizability β were computed. The linear polarizabilities and first hyperpolarizabilities of the studied molecule indicate that the compound can be a good candidate of nonlinear optical materials.

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► Molecular structure of disperse red 1 acrylate molecule was studied using DFT/B3LYP.
► Spectroscopic properties of organic dye molecule were examined by FT-IR, UV and NMR techniques and DFT.
► Isotropic chemical shifts were calculated using the gauge-invariant atomic orbital method.
► Hyperpolarizabilities and HOMO and LUMO energies were performed by DFT approach.