title: Fluorescent acridine-based receptors for H2PO4(-).
abstract: Two new pseudopeptidic molecules (one macrocyclic and one open chain) containing an acridine unit have been prepared. The fluorescence response of these receptors to a series of acids was measured in CHCl(3). Receptors are selective to H(2)PO(4)(-) versus HSO(4)(-), and an even higher selectivity is found over other anions such as Cl(-), Br(-), CH(3)COO(-), and CF(3)COO(-). We show that the macrocyclic receptor is more selective for H(2)PO(4)(-) than the related open chain receptor. The supramolecular interactions of triprotonated receptors with different anions have been modeled in silico and have been studied by different experimental techniques. Optimized geometries obtained by computational calculations agree well with experimental data, in particular fluorescence experiments, suggesting that the selective supramolecular interaction takes places through coordination of the anions to the triprotonated form of the receptor.
authors.affiliation: Department of Inorganic and Organic Chemistry, Universitat Jaume I, E-12070 Castellón, Spain.
authors.forename: Vicente
authors.initials: V
authors.lastname: Martí-Centelles
authors.forename: M Isabel
authors.initials: MI
authors.lastname: Burguete
authors.forename: Francisco
authors.initials: F
authors.lastname: Galindo
authors.forename: M Angeles
authors.initials: MA
authors.lastname: Izquierdo
authors.forename: D Krishna
authors.initials: DK
authors.lastname: Kumar
authors.forename: Andrew J P
authors.initials: AJ
authors.lastname: White
authors.forename: Santiago V
authors.initials: SV
authors.lastname: Luis
authors.forename: Ramón
authors.initials: R
authors.lastname: Vilar
mesh_terms: D000166:Acridines / Q000737:chemistry*; D000838:Anions / Q000737:chemistry*; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000737:chemistry*; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000737:chemistry*
chemical_list: D000166:Acridines; D000838:Anions; D005456:Fluorescent Dyes; D047028:Macrocyclic Compounds; D010756:Phosphoric Acids