Detection and Differentiation of Neutral Organic Compounds by [superscript 19]F NMR with a Tungsten Calix[4]arene Imido Complex

Fluorinated tungsten calix[4]arene imido complexes were synthesized and used as receptors to detect and differentiate neutral organic compounds. It was found that the binding of specific neutral organic molecules to the tungsten centers induces an upfield shift of the fluorine atom appended on the arylimido group, the extent of which is highly dependent on electronic and steric properties. We demonstrate that the specific bonding and size-selectivity of calix[4]arene tungsten–imido complex combined with [superscript 19]F NMR spectroscopy is a powerful new method for the analysis of complex mixtures.National Institute of General Medical Sciences (U.S.) (Grant GM095843)Shanghai Institute of Organic Chemistry (SIOC Postdoctoral Fellowship