Selective binding of 2-anthrylmethylpyrrole with fluoride: fluorescence and theoretical studies

The binding of 2-anthrylmethylpyrrole with halide anions has been investiga ted by means of fluorescence spectroscopy and ab-initio theoretical calcula tions. The synthesized compound exhibits highly selective binding propertie s with fluoride over chloride and bromide, through a preferred hydrogen bon d interaction. The formation of this supramolecular adduct increases the el ectron density on the pyrrole unit which becomes an efficient intramolecula r quencher of the fluorescence of the anthracene moiety via a photoinduced electron transfer process. (C) 2000 Elsevier Science B.V. All rights reserv ed.