In this study, a new tetra-substituted phthalonitrile (diethyl 2-(2-chloro-4,5-dicyano-3,6-bis(hexyloxy)phenyl) malonate) bearing three different substituents was synthesized and characterized. Due to the basic medium, transesterification occurred during the synthesis of the target phthalocyanines [M = Zn (II), Cu (II), Co (II), In (III), Lu (III)] in n-pentanol and the ethyl groups were replaced with pentyl groups. The biological features of the resultant compounds were studied for the first time in this study. All the compounds exhibited high antioxidant, antimicrobial, and DNA cleavage activities. The highest antioxidant activity was obtained 90.39% for lutetium phthalocyanine at 100 mg/L. The most effective MIC value was obtained 8 mg/L against Candida parapisilosis. The most effective microbial cell viability inhibition was obtained 100% for cobalt and lutetium phthalocyanines. They exhibited excellent biofilm inhibiton activities. Higher biofilm inhibition was achieved using light irradiation. The compounds exhibited higher biofilm inhibition activities with photodynamic against Staphylococcus aureus compared with Pseudo aureginosa.