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Sokkalingam, Punidha,Lee, Chang-Hee American Chemical Society 2011 Journal of organic chemistry Vol.76 No.10
<P>A simple, convenient, and inexpensive method has been developed to quantitatively determine fluoride anion concentration in acetonitrile as well as in water. The method exhibited a high selectivity and a great sensitivity toward fluoride anions through “turn-on” chromogenic and fluorogenic dual modes. The fluoride driven silyl deprotection and the subsequent spectral changes of hydroxyl coumarin were the operating foundations for the observed selectivity and sensitivity. <SUP>1</SUP>H NMR spectral titration with F<SUP>–</SUP> revealed that complete deprotection of a triisopropylsilyl (TIPS) group needed exactly 1 equiv of TBAF. UV–vis and fluorescence titration studies exhibited the appearance of a new intense absorption band centered at 434 nm and green emission peak at 500 nm, accompanied by bright yellow color development to the naked eye. An easy-to-prepare test paper, obtained by dipping the paper into the solution of TIPS-protected coumarin derivative, was able to detect F<SUP>–</SUP> in aqueous media. The method has also shown highly promising results in detecting all kinds of fluoride salts, regardless of being organic or inorganic, and thus could be potentially useful in real applications.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/joceah/2011/joceah.2011.76.issue-10/jo200138t/production/images/medium/jo-2011-00138t_0016.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/jo200138t'>ACS Electronic Supporting Info</A></P>
Receptor That Can Capture a Discrete Monohydrated Fluoride Anion
Sokkalingam, Punidha,Kee, Se-Young,Kim, Youngmee,Kim, Sung-Jin,Lee, Phil Ho,Lee, Chang-Hee American Chemical Society 2012 Organic letters Vol.14 No.24
<P>A ‘picket calix[4]pyrrole’ bearing a well-defined binding domain has allowed the stabilization of a monohydrated fluoride anion. The monohydrated F<SUP>–</SUP> was observed only when CsF (not the TBAF) was treated with a host in aqueous acetonitrile. The structure of the receptor-bound, monohydrated F<SUP>–</SUP> was fully characterized by single crystal X-ray diffraction analysis as well as by low temperature <SUP>1</SUP>H and <SUP>19</SUP>F NMR spectroscopy. Further analysis revealed that the complex formed a three-dimensional, salt mediated organic framework in the solid state.</P><P><B>Graphic Abstract</B> <IMG SRC='http://pubs.acs.org/appl/literatum/publisher/achs/journals/content/orlef7/2012/orlef7.2012.14.issue-24/ol302996y/production/images/medium/ol-2012-02996y_0005.gif'></P><P><A href='http://pubs.acs.org/doi/suppl/10.1021/ol302996y'>ACS Electronic Supporting Info</A></P>