In our relentless pursuit of developing innovative antibacterial derivatives, we have successfully generated and evaluated a novel series of 1,2,3-triazole derivatives derived from azo dapsone. The synthesis process commenced with the fusion of the dapsone core with the triazole framework, establishing a solid foundation for our synthetic endeavors. Subsequently, the azo dapsone nucleus underwent functionalization using sodium azide, resulting in the creation of an azide derivative (B). To synthesize the desired end 1,2,3-triazoles, a click reaction was employed, combining the azide compound with triple bond derivatives. The structures of all the synthesized compounds were meticulously characterized through the utilization of advanced techniques such as Nuclear Magnetic Resonance (NMR) and Infrared (IR) spectroscopy. Following the successful synthesis and characterization, our focus shifted to evaluating the in vitro antibacterial activity of these compounds against two significant bacterial strains: the gram-positive bacterium Staphylococcus aureus and the gram-negative bacterium Escherichia coli. Among the compounds synthesized, one compound in particular, designated as (H2), exhibited exceptional potency against Staphylococcus aureus with a minimal inhibitory concentration (MIC) of 25 μg/mL, surpassing the activity of all other prepared compounds. Similarly, compound (H1) displayed remarkable efficacy against Escherichia coli with an MIC of 22 μg/mL, outperforming the other end compounds. These findings demonstrate the tremendous potential of our synthetic approach in generating dapsone derivatives with enhanced antibacterial activity. Our research represents a significant step forward in the development of novel and potent antibacterial agents.