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In recent decades, there has been an increased interest in azo compounds with special optical and biological properties. In this work, we report the preparation of novel azo-compounds with two and three –N=N- double bonds, using the classical method of synthesis, diazotization and coupling. The compounds were characterized by ¹H-NMR, ¹³C-NMR, FTIR, UV-VIS and fluorescence spectra. DFT calculations were employed for determining the optical parameters, polarizability α, the total static dipole moment μ_tot, the quadrupole moment Q and the mean first polarizability β_tot. All azo derivatives show strong fluorescence emission in solutions. The antioxidant and antifungal activities were determined and the influence of the number of azo bonds was discussed. The synthesized compounds exhibit remarkable efficiency in the growth reduction of standard and clinical isolated <i>Candida</i> strains, suggesting future applications as novel antifungal.