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

ABSTRACT: 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 "AB3" 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 A2B2 products are provided.

SUBMITTER: Erdem SS

PROVIDER: S-EPMC2525812 | biostudies-literature | 2008 Jul

REPOSITORIES: biostudies-literature

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

Erdem S Sibel SS Nesterova Irina V IV Soper Steven A SA Hammer Robert P RP

The Journal of organic chemistry 20080530 13

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 fo ...[more]

PMID: 18510363

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