Microwave-assisted Synthesis Of Porphyrins And Kinetics Of Formation Of Porphyrin Complexes

Porphyrins and metalloporphyrins have a broad application in many fields such as medicine,materials science,biomimetic catalysis because of its unique structure and properties.Porphyrins containing fluorine,especially,is a kind of important photosensitizer in Photodynamic Therapy(PDT)for its unique biological activities and the ability of selectively bind to specific tumor tissue.This thesis includes:(1)three mono-fluorine substituted porphyrins were synthesized under microwave condition and kinetics of the formation of metalloporphyrins in acetic acid medium was also investigated.(2)5,10,15,20-tetrakis(4-piperidyl)porphyrin was prepared by means of multistep reaction using isonipecotic acid as starting material and this water-soluble porphyrin’s cell toxicity was studied.Part I:three mono-fluorine substituted porphyrins were synthesized by condensation pyrrole with the corresponding fluorinated benzaldehyde under microwave condition.The best reaction condition was using propionic acid as solvent,nitrobenzene as oxidant and heated for 20 min with 30%microwave power(650W).Although the literature on kinetics of the formation of metalloporphyrins in water,methanol,dichoro-methane,trichloromethane has been reported before,a consideration of kinetics of the formation of metalloporphyrins in acetic acid medium is few and was therefore addressed in this article.Part Ⅱ:Explored the process from starting material isonipecotic acid to 5,10,15,20-tetrakis(4-piperidyl)porphyrin,optimized the reaction conditions and improved the yield of the total reaction.The porphyrins were characterized by nuclear magnetic resonance hydrogen spectrum,infrared spectra,UV-vis spectra and mass spectrometry technology.Preliminary explored the water-soluble porphyrins cell toxicity test,the results found that the water-soluble porphyrin has certain effect to kill cancer cells(OCM-1 cells).