This study reports the synthesis and characterization of two new mono- and di-substituted phthalonitriles namely 4-((9H-carbazol-3-yl)oxy)-5-chlorophthalonitrile and 4,5-bis((9H-carbazol-3-yl)oxy)phthalonitrile, respectively. Cyclotetramerization of the new phthalonitriles in the presence of zinc(ii) acetate resulted in related zinc(ii) phthalocyanines. To study the effect of the position and number of substituents on the biological properties of the phthalocyanines, peripherally or non-peripherally tetra-substituted zinc(ii) phthalocyanines bearing (9H-carbazol-3-yl)oxy groups, as well as axially di-substituted silicon phthalocyanines containing the same groups, were prepared. Since gold nanoparticles are well-known as efficient drug delivery agents, the surface of these metal nanoparticles was functionalized with all the compounds. This modification also improved the solubility of the phthalocyanines in aqueous media. In this study, the antioxidant, DNA cleavage, and toxic/phototoxic activities of the resultant nanoconjugates were examined. With a combination of metal ion and substituent (nature, number, and position) effects, the silicon(iv) phthalocyanine exhibited the highest biological properties.