A new fluorogenic probe for fluoride anion detection was designed and synthetized accomplishing by the linkage between a Coumarin-440 and a Boc-Ser(TBDMS)-OH via amide bond formation. The photophysical properties and the selectivity for fluoride detection, among a range of anions (Cl-, Br-, I-, BF4 -, NO3 -, ClO4 -, PF6 -, HSO4 -, CN-, OAc-), was explored. The sensing mechanism was proposed and supported by 1H NMR and MALDI-MS experiments. A reaction triggered by the nucleophilic attack of the fluoride anion to the silicon atom of the tert-buthyldimethylsilane (TBDMS) group was responsible for the disruption of OSi bond, which generates an emissive species. UV-vis absorption, fluorescence steady state, and time resolved emission spectroscopy were employed. The lowest quantity of detectable amount of 3.3 μmol/L for F- was achieved for fluorescence measurements in acetonitrile solution. The system could be adapted to paper discs under a UV lamp (365 nm) for direct visual fluoride ion detection.
|Number of pages||7|
|Journal||Dyes and Pigments|
|Publication status||Published - Dec 2016|
|Event||2nd International Caparica Congress on Chromogenic and Emissive Materials (IC3EM) - Caparica, Portugal|
Duration: 5 Sep 2016 → 8 Sep 2016
Conference number: 2nd
- Tert-butyldimethyl silane