In the present work, four electrophilic group substitute phenyldiazenyl derivatives were synthesized using an electrophilic substitution reaction. The physicochemical analysis was carried out using FT-IR, 1H NMR, and HR-MS data. The photophysical studies were carried out using theoretical methods. Density functional theory was employed to illustrate the electronic and optical characteristics of the synthesized compounds. The HOMO-LUMO energies were theoretically computed in different solvents using Gaussian 09W software and results are compared with the experimental values. The molecule PT4 shows highest bandgap of 4.497eV. Further, the global chemical reactivity descriptors were used to determined nature of chemical reactivity. The GCRD parameters reveal the high electrophilic behaviour of PT3 and PT3. Further, the effectiveness of the colorant anti-tubercular activity was evaluated using invitroand molecular docking techniques. The biological activity results reveal that barbituric acid coupled with phenyldiazenyl displayed excellent anti-tubercular activity compared with the standard Gentamycin.