Preparation and photoactivity of a novel water-soluble, polymerizable zinc phthalocyanine

A novel water-soluble and polymerizable photosensitizer, zinc tetra(N-carbonylacrylic)aminophthalocyanine (Zn-MPc), was synthesized by the ornament of zinc tetraaminophthalocyanine (Zn-APc) with maleic anhydride and characterized by 1H NMR, FT-IR, and MALDI-TOF mass spectra. The photoactivity of Zn-MPc was determined by tracking the degradation of 1,3-diphenylisobenzofuran (DPBF). The results indicated that Zn-MPc is an efficient photosensitizer and has a high photostability. The apparent rate constant, ka, of DPBF photodegradation increased with the increase of the Zn-MPc concentration or light intensity, but declined with the increase of the initial concentration of DPBF. Furthermore, the kinetics equation was deduced as Rd = 1.12 × 10−5[DPBF]0.51[Zn-MPc]0.54E1.35. The results in this work provide a basis for the further development of more desirable phtotosensitizers and their applications in photodynamic therapy (PDT) of cancer.

Graphical abstractModification of zinc tetraaminophthalocyanine with maleic anhydride afforded a water-soluble, polymerizable zinc tetra(N-carbonylacrylic)aminophthalocyanine. It is an efficient photosensitizer in terms of the rate of DPBF degradation and the photostability. The kinetics equation of the initial degradation rate of DPBF is Rd = 1.12 × 10−5[DPBF]0.51[Zn-MPc]0.54E1.35, which can provide a novel thought for the application of photosensitizers in PDT and the design of other efficient photosensitizers.Figure optionsDownload full-size imageDownload as PowerPoint slide