Work

Solid-Phase Synthesis of Asymmetrically Substituted “AB3-Type” Phthalocyanines

Year: 2008

Type: article

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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo800536v

Authors: S. Sibel Erdem, Irina V. Nesterova, Steven A. Soper, Robert P. Hammer

Institution: Louisiana State University

Language: English

Topic: Porphyrin and Phthalocyanine Chemistry

Subfield: Materials Chemistry

Field: Materials Science

Domain: Physical Sciences

Open Access status: green

Funders: National Human Genome Research Institute, National Cancer Institute, National Institute of Biomedical Imaging and Bioengineering, Division of Chemistry

Awards: G1571270626, G1976738804, Modular Microfluidic System for Automated DNA Sequencing, Microsampling Unit for Capturing Low Abundant Cells, High Throughput Modular Microfluidic Systems for Drug Discovery/Development