Firstly, 4-(4-carboxyl group)-O-benzene phthalonitrile (CPPN) and quinolineoxy-phthalonitrile (QPN) were prepared by reacting 4-nitrophthalonitrile with p-hydroxybenzoic acid and 8-hydroxyquinoline respectively. Then, the silica gel was bonded with phthalonitrile CPPN-PGMA/SiO₂ was obtained by the ring opening reaction between CPPN and polyglycidyl methacrylate-modified silica (PGMA/SiO₂). Finally, the phthalocyanine was synchronously synthesised and immobilized onto CPPN-PGMA/SiO₂ through the reaction between CPPN-PGMA/SiO₂ and QPN and the metal salts(Co(CH₃COO)₂·4H₂O) of them were characterized by FT-IR, SEM, and TG. And their UV-visible diffuse reflectance spectra were determined. The effect of the dosage of catalyst DBU on the immobilized reaction of phthalocyanine was investigated. Finally, with the organic dye methylene blue (MB) as target degradation material, the photocatalytic properties of immobilized phthalocyanine catalyst QPc-PGMA/SiO₂ and CoQPc-PGMA/SiO₂ were researched. The results show that phthalocyanine could be immobilized onto PGMA/SiO₂ successfully by the method of synchronous synthesis and immobilization, obtaining the immobilized photocatalyst QPc-PGMA/SiO₂ and CoQPc-PGMA/SiO₂. Moreover, both CoQPc-PGMA/SiO₂ and QPc-PGMA/SiO₂ can effectively catalyze the degradation of MB under visible light irradiation. And the degradation rate of MB increases with the increasing concentration of CoQPc-PGMA/SiO₂. Moreover, the catalytic degradation of MB by CoQPc-PGMA/SiO₂ at lower concentration was better than that by QPc-PGMA/SiO₂ under visible light irradiation. Alkaline conditions were beneficial to the photocatalytic degradation of MB by CoQPc-PGMA/SiO₂. When the pH is 10.0, 0.2 g/L CoPc-PGMA/SiO₂ could make the degradation rate of MB up to 97%. The properties of the peripheral substituents of immobilized phthalocyanines have a certain effect on the photocatalytic degradation of phenol, and the photodegradation of phenol by CoQPc-PGMA/SiO₂ with donor electron conjugation effect is the best, and its degradation rate of phenol reaches 58% in 5 min and 100% in 2 h. In addition, immobilized metal phthalocyanines have good reusability.