Synthesis of Asymmetrical 5,10,15-Tri(p-chlorophenyl)-20-(p-methoxy)Phenyl Porphyrin

Asymmetrical porphyrins structure widely exists in heme, chlorophyll A, vitamin B₁₂, and other natural products, and plays a vital role in photodynamic therapy of cancer, mimic catalysis , solar cell materials and so on. Generally, A₃B-type porphyrin, which belongs to an asymmetric porphyrins, is synthesized by the Little and Linsey method. In this work, we synthesized the asymmetrical 5,10,15-tri(p-chlorophenyl)-20-(p-methoxy)phenyl porphyrin. Compared with our previous study, the procedure was further optimizated, which mainly involved a systematic investigation for the reaction conditions for the A₃B-type asymmetrical porphyrin, such as solvent effect, reactor and so on, demonstrating that solvent effect shown a critical influence to the yield and selectivity of the asymmetrical A₃B-type porphyrin. After optimizing, the total yield of porphyrins was 12.7%, and the selectivity and yield of the asymmetric pophyrin were 45.7% and 5.8%, respectively. This work was financially supported by the National Natural Science Foundation of China (nos. 21276006, 21476270).