Terpene-macrocycle conjugates, consisting of thymol or carvacrol and phthalocyanine were synthesized, characterized, and subjected to detailed optical and biological studies. The macrocyclization reactions of terpene-substituted o-phthalonitrile derivatives were performed in a microwave reactor to give thymol- and carvacrol-phthalocyanine conjugates, which were carefully purified by column chromatography and subsequently analyzed using HPLC and characterized using UV–Vis, NMR and MS. Both isolated phthalocyanine derivatives represent isomers of C2v symmetry, which was confirmed by NMR study. The absorption UV–Vis spectra of studied thymol- and carvacrol-phthalocyanine conjugates with the Soret and the Q band possesses the same profile. Both molecules reveal emission in the red region of the spectrum with fluorescence quantum yields about two-fold lower in DMF and significantly lower in DMSO than that observed for zinc(II) phthalocyanine. The analyzed phthalocyanine derivatives generate singlet oxygen upon excitation with light at ca. three-fold lower level then that noticed for zinc(II) phthalocyanine. In comparison to zinc(II) phthalocyanine, both molecules also reveal two-fold lower photostability in DMF and similar stability in DMSO. Thymol- and carvacrol-phthalocyanine conjugates, zinc(II) phthalocyanine, thymol, and carvacrol were loaded into modified liposomes and subjected to biological activity study. Thymol-phthalocyanine conjugate at both 100 and 10 µM revealed high, ca. 5 log photoinactivation potential on the growth of Enterococcus faecalis, similarly to reference zinc(II) phthalocyanine. For carvacrol-phthalocyanine conjugate, an increase of photoinactivation activity was observed at only 100 µM in comparison to zinc(II) phthalocyanine, whereas a decrease at the concentration of 10 µM was noticed. It is crucial that both studied phthalocyanines cross the border of 3 log photoinactivation potential, which indicates their bactericidal potential. In the Microtox® bioassay both conjugates revealed significantly decreased dark toxicity in comparison to thymol and carvacrol only. Interestingly, the carvacrol-phthalocyanine conjugate was found to be more toxic in comparison to thymol-phthalocyanine conjugate and zinc(II) phthalocyanine.