This study reports the 3 new phthalonitrile derivatives, namely 4, 5 Bis-[4-(4-bromophenoxy) phenoxy] phthalonitrile (
1
), 4,5 Bis-[4-(4-chlorophenoxy) phenoxy]phthalonitrile (
2
), and 4, 5 Bis[4-(4-fluorophenoxy) phenoxy] phthalonitrile (
3
). Their octa-substituted zinc phthalocyanines (
4
,
5
,
6
) are reported for the first time in this study. The resulting compounds were characterized by utilizing some spectroscopic methods, such as UV-Vis, 1HNMR, FT-IR spectroscopy, as well as mass spectraand elemental analysis. To show photosynthesizer’s potential, emission (F
F
), singlet oxygen (1O2), and photodegradation quantum yields (F∆, Fd) of octa-peripherally phthalocyanines (Pcs) were performed in the solutions, such as biocompatible solvent DMSO (dimethyl sulfoxide) as well as DMF (dimethylformamide) and THF (tetrahydrofuran). Solvent and octa-peripherally binding effect of the halogen (Br, Cl, F) terminated phenoxy-phenoxy groups on phthalocyanine rings for photophysicochemical properties (
4
,
5
, and
6
) were compared with the tetra-peripherally and tetra nonperipherally substituted derivatives. The new dyes (
4
to
6
) may be evaluated in photodynamic therapy (PDT) of cancer as photosensitizers due to efficient 1O2 from 0.55 to 0.75.
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