Molecular structure, spectroscopic investigations, second-order nonlinear optical properties and intramolecular proton transfer of (E)-5-(diethylamino)-2-[(4-propylphenylimino)methyl]phenol: A combined experimental and theoretical study

This work presents a combined experimental and theoretical study on an ortho-hydroxy Schiff base compound, (E)-5-(diethylamino)-2-[(4-propylphenylimino)methyl]phenol. The crystal structure and spectroscopic properties of the compound have been determined by using X-ray diffraction, IR and UV–vis spectroscopy techniques. The electronic structure, vibrational frequencies and electronic absorption spectra have been investigated from the calculative point of view. A relaxed potential energy surface scan has been performed based on the optimized geometry of OH tautomeric form to describe the potential energy barrier belonging to intramolecular proton transfer and to observe the effects of transfer on the molecular geometry. The second-order nonlinear optical properties have been investigated based on the first static hyperpolarizability (β) by using the density functional theory.

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► Asymmetric unit of title compound contains two independent identical molecules.
► Indicative bond lengths and HOMA indexes show that the molecules display OH form.
► Potential energy barrier was determined as 4.957 kcal mol−1.
► Title compound can be a good applicant in the development of NLO materials.