Solid-Phase Synthesis of Asymmetrically Substituted 'AB3-Type' Phthalocyanines

Autor:	Irina V. Nesterova, S. Sibel Erdem, Steven A. Soper, Robert P. Hammer
Rok vydání:	2008
Předmět:	Indoles Molecular Structure Nitrile Organic Chemistry Chemical synthesis Article Phthalonitrile chemistry.chemical_compound Solid-phase synthesis chemistry Polymer chemistry Phthalocyanine Trifluoroacetic acid Coloring Agents Ethylene glycol Linker
Zdroj:	The Journal of Organic Chemistry. 73:5003-5007
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo800536v
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::4383a2c308e32208d2e13ee4c40db5ac https://doi.org/10.1021/jo800536v Zobrazit plný text záznamu