4,4-Nitrophenoxyaniline derived Azo ester: Structural elucidation, DFT simulation, and DNA interactional studies via wet and in silico methods

•A new ester molecule is synthesized by classical condensation method.•Characterization by Spectroscopic techniques and Single crystal analysis.•DFT simulation for structural elucidation.•DNA binding studies by multi techniques. A new ester namely,1-((4-(4-nitrophenoxy)phenyl)diazenyl)biphenyl benzoate, has been synthesized by esterification reaction between reported nitro terminated azo alcohol and benzoyl chloride. Complete structural elucidation of the synthesized ester was done by different spectroscopic techniques including (FT-IR), (Proton and Carbon-13 NMR), (UV/VIS) spectroscopy, and single-crystal XRD analysis and cyclic voltammetry. XRD structural elucidation revealed the ester 1a to be in Triclinic crystal system with P-1 space groups, showing two-dimensional supramolecular structure, involving only one intermolecular interaction between O4-O9…H9. DFT simulations were also performed to illustrate structural ramification of synthesized ester. Further, Drug DNA interaction was used to determine the biological significance of the produced ester. UV–VIS spectroscopy, hydrodynamic measurement, and molecular docking were used to determine the preferred binding mode of interaction of the synthesized ester with Salmon Sperm (SS) DNA and found that molecule interacts in groove binding fashion with DNA molecule. 2021 Elsevier Ltd. All rights reserved. [Display omitted]