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  • Title: Fluoride recognition by a chiral urea receptor linked to a phthalimide chromophore.
    Author: Pérez-Ruiz R, Díaz Y, Goldfuss B, Hertel D, Meerholz K, Griesbeck AG.
    Journal: Org Biomol Chem; 2009 Sep 07; 7(17):3499-504. PubMed ID: 19675906.
    Abstract:
    The anion chemosensor 1 based on a urea-activated phthalimide with a stereogenic centre was synthesized using an efficient procedure involving a Curtius rearrangement. Its photophysical properties were estimated in several solvents. Sensor 1 detected fluoride with absorption as well as fluorescence changes and was only observable for this case and not for other halides. The appearance of a new CT complex emission at a longer wavelength and no changes in the singlet lifetime of 1 in the presence of fluoride supported a fluorescence static quenching mechanism. 1H-NMR studies, together with theoretical calculations based on DFT methods at the B3lYP/6-31G* level of theory confirmed the formation of a [1-F]- complex through H-bonding interactions rather than receptor deprotonation in the recognition process. Reversibility of this process was observed upon addition of a protic solvent.
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