4.6 Article

Fluoride recognition by a chiral urea receptor linked to a phthalimide chromophore

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ORGANIC & BIOMOLECULAR CHEMISTRY
卷 7, 期 17, 页码 3499-3504

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ROYAL SOC CHEMISTRY
DOI: 10.1039/b908433a

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  1. Alexander von Humboldt Foundation
  2. DAAD

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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. H-1-NMR studies, together with theoretical calculations based on DFT methods at the B31YP/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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