期刊
JOURNAL OF FLUORINE CHEMISTRY
卷 129, 期 10, 页码 961-967出版社
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2008.05.009
关键词
Fluorous; Ion-selective electrode; Potentiometry; Phase-transfer catalyst; Perfluorinated acids; Phosphonium
资金
- National Science Foundation [CTS-0428046]
- National Institutes of Health [1R01 EB005225-01]
Fluorous solvents are the most nonpolar, nonpolarizable phases known, whereas ions are inherently polar. This makes it difficult to create salts that are soluble in a fluorous solvent. Here we present the synthesis and characterization of a new fluorophilic phosphonium salt, tris{3,5-bis[(perfluorooctyl)propyl]phenyl}methylphosphonium methyl sulfate. The salt has a solubility of at least 14 mM in perfluoro(perhydrophenanthrene), perfluoro(methylcyclohexane), and perfluorohexanes. It also shows immediate potential for use as a phase-transfer catalyst in fluorous biphasic catalysis, but in this work it is used as an anion-exchanger site in the first potentiometric fluorous-membrane anion-selective electrode. The membrane sensor exhibited the exceptional selectivity of 3.9 x 10(10) to 1 for perfluorooctanesulfonate over chloride, and of 2.5 x 10(7) to 1 for perfluorooctanoate over chloride. With improvements to the sensor's detection limit and lifetime, it has the potential to be an attractive alternative to the expensive, time-consuming methods currently employed for measurement of perfluorinated acids. (C) 2008 Elsevier B.V. All rights reserved
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