Synthesis of Amphiphilic Phthalocyanine Derivatives and Their Cyclic Voltammetry
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概要
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Phthalocyanine analogues containing alkyl-substituted benzenoid rings and pyridine rings are interesting compounds, because quaternation of the pyridine nitrogen is expected to form cationic amphiphilic compounds. <BR>Non peripheral long alkyl substituted zinc phthalocyanine derivatives, zinc bis (1, 4-didecylbenzo) -bis (3, 4-pyrido) porphyrazine and zinc bis (1, 4-didecylbenzo) -bis (2, 3-pyrido) porphyrazine were reacted with dimethyl sulfate and monochloroacetic acid to give their quaternary products. Also the zinc phthalocyanine derivatives reacted with diethyl sulfate to afford the sufo-substituted products. All reacted compounds showed amphiphilic character. <BR>Regio isomers of zinc bis (1, 4-didecylbenzo) -bis (3, 4-pyrido) porphyrazine were also quaternized with dimethyl sulfate. <BR>Identical peaks in cyclic voltammograms appeared for the products before and after quaternation. It was thought that there was no effect of the quaternation of zinc bis (1, 4-didecylbenzo) -bis (3, 4-pyrido) porphyrazine or zinc bis (1, 4-didecylbenzo) -bis (2, 3-pyrido) porphyrazine on the redox properties of phthalocyanione analogous, because redox potentials did notchange. <BR>Regio isomers of zinc bis (1, 4-didecylbenzo) -bis (3, 4-pyrido) porphyrazine was reacted with dimethyl sulfate to give the corresponding methylated regio isomers. <BR>Cyclic voltammograms of the regio isomers were measured under the same condition for before and after the quaternation. The shapes of the cyclic voltammograms of quaternized regio isomers was the same as that of the corresponding non quaternation derivatives. After quaternation of regio isomers, the peaks of cyclic voltammograms were emphasized, which suggested that the photoelectron transfer ability was kept unchanged regardless of the quaternation.
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