ORGN 210 |
| The switching of molecules from a hydrocarbon (HC) phase to a perfluorocarbon (PFC) phase is typically achieved by the covalent attachment of long perfluoroalkyl chains. Taking advantage of labile coordination bonds, we have developed a reversible HC/PFC phase-switching protocol that relies on the reversible coordination of pyridyl tags to a “heavy fluorous” dicopper(II)-carboxylate complex that is soluble in PFCs only. Of particular interest is the extreme efficiency and sensitivity of this reversible “catch-and-release” process. For example, quantitative release in the organic phase is achieved simply by adding THF to the biphasic system. Application of this methodology to the reversible phase-switching of pyridyl-tagged porphyrins/metalloporphyrins, substrates/products and for the development of an “indicator-displacement assay” for the sensing of analytes such as histamine will be presented. |
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Recent Advances in Fluorous Chemistry
8:00 AM-12:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Ballroom C, Oral
Division of Organic Chemistry |