Concise experimental and DFT study of newly synthesized 5,17-di(2-antracenylazo)-25,27-[1,3-ethylene-bis(aminocarbonylmethoxy)]-26,28-dihydroxycalix[4]arene

• A derivative of calix[4]arene is synthesized. • It is experimentally characterized by FT-IR and 1 HNMR. • Computational study is performed at B3LYP/6-31G(d) and mPW1PW91/6-31(d,p) levels. • Total and partial densities of states are calculated. • Results of computational study matches with corresponding ones of experimental study. In this work, 5,17-di(2-antracenylazo)-25,27-[1,3-ethylene-bis(aminocarbonylmethoxy)]-26,28-dihydroxycalix[4]arene has been synthesized by using 5,17-di(2-antracenylazo)-25,27-di(ethoxycarbonylmethoxy)-26,28-dihydroxycalix[4]arene. The solid phase FT-IR spectra of the title molecule have been recorded in the region of 400–4000 cm -1 . The equilibrium molecular geometry, harmonic vibrational frequencies and infrared intensities of studied molecule are calculated by density functional theory with B3LYP/6-31G(d) and mPW1PW91/6-31(d,p) levels. Moreover, 1 H NMR chemical shifts are calculated by employing the Gauge Independent Atomic Orbital (GIAO) method via utilizing the same methods for studied molecule in this work. The total and partial densities of states of the title molecule are analyzed via GaussSum 3.0 program. The electronic properties, such as HOMO and LUMO energies, HOMO-LUMO band gaps and molecular electrostatic potential surface of the molecule have been calculated at the levels of B3LYP/6-31G(d) and mPW1PW91/6-31G(d,p). Additionally, Natural Bond Orbital (NBO) analysis was performed to investigate intramolecular charge transfer, electron density delocalization, and donor–acceptor interactions in the molecule. Furthermore, to provide a deeper understanding of the molecule’s electronic behavior and potential non-linear optical (NLO) performance, key NLO parameters, including dipole moment, polarizability, and first hyperpolarizability, were calculated. The calculated results are compatible with the corresponding experimental values.