Dissertation > Industrial Technology > General industrial technology > Materials science and engineering > Functional Materials

Synthesis, Property and Photodynamic Activity of Soluble Phthalocyanines

Author WeiShaoHua
Tutor HuangDeYin
School Shanghai Jiaotong University
Course Materials Science
Keywords soluble phthalocyanines synthesis spectrum property aggregation solvent effect photodynamic activity
Type PhD thesis
Year 2006
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Phthalocyanines are a kind of organic compounds with multi-function and multiple usage, they are becoming a new indispensability functional material nowadays. Inquiring the relation among the structures, properties and functions of phthalocyanines has very important significance theoretically and practically. The present dissertation is aimed to design and synthesize a series of soluble phthalocyanines with dissimilar structures, to examine the correlation between structure and basic properties, and the influence rules of environments to the properties. Based on the above results, the photodynamic property and action mechanism of amphiphilic phthalocyanine were studied. Main research results are as follows:1. Synthesization and soluble characteristic of compoundsFive phthalonitrile derivatives, which have been substituted by the ArO or the RO group, and nine soluble phthalocyanines were designed and synthesized. All of those intermediates and products were characterized by element analysis, UV spectra, IR spectra and 1H-NMR. Among these compounds, 4-(3-trifluoromethylphenoxy)-phthalonitrile, 4-(5-sulfo-1-naphthoxy)-phthalonitrile, FPcH, FPcNi, FPcCo, FPcZn, FPcVO and LSPcZns are new compounds, and have not been reported in other papers. The results of experiments suggested that LSPcZn was one kind of phthalocyanine which has amphiphilic. Other compounds have good soluble properties in the weak polar and medium polar solvents.2. Spectrum property(1) Comparing with none substituted phthalocyanines, introducing of the ArO or the RO group can make theλmax of metal phthalocyanines red shift for certain degree, and red shift degree of the RO group substituted phthalocyanines was bigger than that of the ArO group substituted phthalocyanines. With the increase of the electron obtaining ability of the substituted group of ArO group, itsλmax shifts toward the shorter wave length. With the increased number of d electron of the center metal ion, itsλmax shifts toward the longer wave length, where the order is VO>Zn>Ni> Co. The weak absorption of Q band at 605

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