A symmetrical azo-based Luminol derivative 2 was synthesized using catalytic dehydrogenative coupling reaction procedure. This symmetrical molecule shows blue fluorescence in polar aprotic solvents (λ_max = 450 nm). With an increase in aqueous content 2 was exhibiting aggregation caused fluorescence quenching (ACQ) with a red shift of 30 nm (λ_max = 480 nm). Distinct emission features were observed for this molecule with a variation in the pH range. In basic medium, deprotonated form of 2 shows fluorescence quenching followed by enhancement of green chemiluminescence (λ_max = 490 nm) with H₂O₂/Fe³⁺catalytic system. The fluorescence and chemiluminescent (CL) properties of 2 were compared with its parent luminol 1, The CL emission intensity of 2 was found to be about 16 times higher than that of 1. In addition, HOMO-LUMO energy gap for 2 was also calculated using density functional theory (DFT) studies.