The Synthesis Of Several New Phthalocyanines And Their Application In Photodynamic Therapy Of Cancer

The phthalocyanine and its derivatives which have extraordinary properties of chemical and thermal stability,intense coloration and photostability,due to its planar structure of 18π- electron conjugation,have appealed great interests of scientists.By modifying and changing the central atom and peripheral substitutions,the scientists synthesized many different types of new phthalocyanine and explored their applications in photodynamic therapy,optical information recording medium,solar cells and nonlinear optical materials.As a photosensitizer in photodynamic therapy of cancer,phthalocyanine is considered as the most promising compound to take the place of the photofrin.This work has designed a kind of para-hydroxyphenoxy phthalocyanine and synthesized a compound with low aggregation and amphiphilic properties.By using two different kinds of methods,four α-4-hydroxyphenoxy phthalocyanines have been synthesized which have different central atoms.In order to compare the different sites of the molecular affecting their aggregation trend,β-(4-OH-PhO)4-ZnPc andβ-(4-OH-PhO)4-H2Pc were synthesized.The hydroxyphenoxy substitution has made the molecular solve in both organic solvent and alkaline water.The benzene ring at theαsite increased the steric effect and decreased the aggregation.All these compounds are characterized by IR,NMR,MS,UV-Vis (except theα-(4-OH-PhO)4NiPc which can hardly gain an exact H1-NMR).The photophysical properties have been investigated by fluorescence, UV-Vis and time-resolved single photon counting,mainly focused on theα-(4-OH-PhO)4ZnPc which has good properties in photodynamic therapy. The fluorescence quantum yield and lifetime have been measured comparing with the similar moleculars.The main reason of the decline of the fluorescence quantum yield and lifetime is because of photoinduced intramolecular electron transfer process.The participation of oxygen in photodynamic therapy of cancer is an essential pathway.This thesis have investigated the interaction between theα-(4-OH-PhO)4ZnPc and the oxygen by detecting the production of superoxide anion(TypeⅠ)and measuring the quantum yields of singlet oxygen formation(TypeⅡ).Finally we conclude that theα-(4-OH-PhO)4ZnPc is an promising TypeⅠphotosensitizer which is different from the traditional TypeⅡphotosensitizer.