Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 13, Pages 2535-2541Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201200140
Keywords
Heterocycles; Fluorides; Silyl ethers; Fluorescent probes
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Funding
- Deutscher Akademischer Austausch Dienst (DAAD)
- National Council for Scientific and Technological Development (CNPq) [304887/2010-2]
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This work describes the synthesis of five O-silyloxy-1,3-thiazoles and their use as fast-response turn-on probes for fluoride ion detection in polar aprotic solvents and in aqueous cetyltrimethylammonium bromide micellar medium. The fluoride-triggered deprotection of these silyl ethers results in ca. 180-nm shifts in the fluorescence emission wavelengths. All compounds are suitable for the detection of fluoride ions with a detection limit in DMSO of 107 mol?L1; derivatives containing a 2-pyridyl moiety in the thiazole system are more efficient than those with a 3- or 4-pyridyl moiety. Typical anionic interferents, such as acetate or chloride, are not detected by O-silyloxy-1,3-thiazoles, making these compounds very specific for fluoride.
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