This work describes the synthesis, spectral, aggregation and fluorescence properties of bis 4-[(4-tert-butylbenzyl) oxy substituted metal free (2), magnesium (3), zinc (4) and nickel (5) phthalocyanines. The syntheses of the novel compounds were confirmed by FT-IR, UV-vis, mass and NMR spectroscopy techniques, as well as elemental analysis. The effects of the nature of the central metal on the photophysical parameters of the phthalocyanine complexes are reported in this study. The photochemical properties (singlet oxygen quantum yields and photodegradation quantum yields) and photophysical properties (fluorescence behavior and fluorescence quantum yield) of the complexes were reported in different solutions (dimethyl sulfoxide (DMSO) and dimethyl formamide (DMF) and tetrahydrofuran (THF)). However, energy minimized structure, vibrational frequency, molecular orbital levels and electronic absorption spectra were obtained by DFT calculations which supported the experimental results.