Solid-phase synthesis of asymmetrically substituted "AB3-type" phthalocyanines

被引：39

作者：

Erdem, S. Sibel ^{[1
]}

Nesterova, Irina V. ^{[1
]}

Soper, Steven A. ^{[1
]}

Hammer, Robert P. ^{[1
]}

机构：

[1] Louisiana State Univ, Dept Chem, Baton Rouge, LA 70803 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 13期

关键词：

D O I：

10.1021/jo800536v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of phthalocyanines with asymmetrical substitution on the periphery is often difficult due the problems in purification of the phthalocyanine mixtures obtained. Using a poly(ethylene glycol) (PEG)based support with a Wang-type linker, we have developed the synthesis of monohydroxylated, oligoethylene glycol substituted phthalocyanines utilizing an amidine-base-promoted phthalonitrile tetramerization reaction. The use of a hydrophilic support allows symmetrical phthalocyanine product formed in solution to be readily and completely removed by washing while leaving the "AB(3)" product on the support. Acid cleavage with 10% trifluoroacetic acid provides the pure unsymmetrically substituted Pc. This method was applied to several metallo Pcs. Additionally, methods to avoid premature reactions on-resin that give A(2)B(2) products are provided.

引用

页码：5003 / 5007

页数：5

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