Study On Synthesis, Separation And Photophysical Chemical Properties Of An Amphiphilic Phthalocyaninatozinc

In our previous studies, it was found that an amphiphilic phthalocyaninatozinc, disulfonated diphthalimidomethyl phthalocyaninatozinc (ZnPcS2P2, where S and P were the sulfonate and phthalimidomethyl groups respectively), had higher PDT activities and less photosensitive toxicity than the clinical Photofrin? that is prevalent at present. But, in its synthesis, the P and S groups were introduced to the phthalocyaninatozinc (ZnPc) by a 'one pot' method that led to their products with too many components to be separated and purified. To reduce the number of components, we alternated the synthesis rout from the P and S group substituted phthalonitriles. Therefore, the 4-phthalimidomethyl phthalonitrile was firstly synthesized from 4-methyl phthalic anhydride by five-step reaction. And potassium 4-sulfophthalonitrile was synthesized from 4-nitrophthalonitrile also with five steps. Then the mixtures ZnPcSnP4-n were obtained by statistic condensation method or "half phthalocyanine" method. It is found that their yields and reproducibility from the phthalonitrile derivatives are relative higher than either of a 'one pot' method or from P and S group substituted phthalic acids. Simultaneity, from the characterized data of ZnPcS2P2, it could speculate out that the P and S groups in ZnPcS2P2-A might be arranged clockwise. The photophysical chemical properties and anti-tumor activity of this component all showed a good PDT photosensitivity. In addition, in order to improve the separation efficiency of ZnPcS2P2, the stationary phase for HPLC bonded with phthalocyanines was also prepared and investigated in this dissertation. The results showed that, the stationary phase bonded with (tri-β-2,4-ditertbutylphenoxy-β-sulfonamide)phthalocyaninatocopper is effective to separate some kinds of phthalocyanines, but it is not adaptive to the ZnPcS2P2. Furthermore, the constitutes and isomer distributions of tetrakis(2,2,4-trimethyl-3-pentoxy)phthalocyaninatopalladium from different synthetic methods had also been investigated. And the photophysical chemical properties of some phthalocyaninatopalladiums had been discussed, which showed that although the center ion palladiums with open-shell electron structures, their PDT activities were close to phthalocyaninatozincs whose hold close-shell electron structures.