Abstract
•Two new azo based compounds were synthesized and characterized by Spectro analytical techniques.•The intermolecular interactions in compounds 1 and 2 were investigated by Hirshfeld surface analysis.•The results of DPPH activity indicate that the azo compounds exhibit moderate scavenging activity compared to ascorbic acid the enhancement in biological activities was attributed to the tributyl groups linked to the tin atom.•The photochemical isomerization behavior of compound 1 shows a reversible trans–cis isomerization upon photo-irradiation of UV light.•The FMOs and MEPs as calculated through quantum chemical calculations are used to explain ground state electronic charge distributions and reactivity tendencies among both compounds.
In search of achieving some specific fluorescent and biological applications, azo-based compounds 1 and 2 with robust H-bonding and strong peptide properties were synthesized and characterized by essential spectroscopic techniques such as UV–Vis, FT-IR, 1H NMR, and single-crystal X-ray crystallographic studies. The intermolecular interactions in compounds 1 and 2 are elaborated by Hirshfeld surface analysis. Both compounds exhibit maximum absorption between 250 and 400 nm in the trans configuration with allowed transitions. Irradiating the solution of compound 1 with UV light, the intensity of the peaks around 285 and 339 nm changed with time indicating the isomerization from trans to cis state. The antioxidant activity of compounds 1 and 2 was studied by using the DPPH free radical scavenging assay with fixed reaction time and steady-state measurements. The results indicate that the azo compounds exhibit moderate scavenging activity compared to ascorbic acid. As a result of DNA interactions, a hypochromic shift was observed in the UV–Vis spectra of compounds 1 and 2 at different concentrations of DNA. The values of binding constant (Kb) and Gibbs free energy (ΔGo) for compounds 1 and 2 were found to be 1.5 × 104 M–1, -23.8 kJ/mol and 1.9 × 104 M–1 and -22.8 kJ/mol, respectively. Additionally, compounds 1 and 2 were docked with different DNA fragments to get structure-property insights by studying the intermolecular interactions of their respective complexes. The binding interaction energies of compounds 1 and 2 are found to be -8.40 and -7.70 kcal/mol for 1BNA (DNA) fragment and -8.50 and -7.90 kcal/mol for 1D29 (DNA), respectively. To get molecular-level structural insights, the frontier molecular orbitals (FMOs) and molecular electrostatic potentials (MEPs) were also calculated and explained for the optimized molecular geometries of compounds 1 and 2. The current combined experimental and computational study highlights the importance of our synthesized compounds which may evoke the scientific interest of the chemical community to further explore their potential in-vivo and in-vitro applications.
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