Novel water-soluble metallophthalocyanines (M: Co, Ni, Cu, Zn) containing azo dye were characterized. The structures were confirmed by IR, UV/vis, H-1 NMR, C-13 NMR, mass spectroscopy, and elemental analysis. Photochemical properties and aggregation behavior of zinc phthalocyanines were investigated. Singlet oxygen quantum yields of the zinc phthalocyanines (2d, 3d, 5d, and 6d) were 0.8, 0.57, 0.71, and 0.46, respectively.