期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 73, 期 13, 页码 5003-5007出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo800536v
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资金
- NCI NIH HHS [R33 CA099246-03, R33 CA099246] Funding Source: Medline
- NHGRI NIH HHS [HG01499, R01 HG001499] Funding Source: Medline
- NIBIB NIH HHS [EB006639, R01 EB006639] Funding Source: Medline
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.
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