title: Synthesis, structural characterization, experimental, and computational spectrophotometric studies of 8-quinolinyloxymethyphosphonate compounds.
abstract: The synthesis of diethyl-8-quinolinyloxymethylphosphonate 1 and 8-quinolinyloxymethylphosphonic acid hemihydroiodide 2 is reported along with their spectroscopic and analytical characteristics (NMR, infrared, mass spectra, and elemental analysis). The single-crystal X-ray structure of 2 is described. Solutions of the disodium phosphonate 3, from 2 and sodium hydroxide, were prepared and used in situ. The coordination complex between 1 and zinc chloride 4 is described according to its single-crystal X-ray structure. The spectrophotometric features (absorption and emission) of 1, 2, 3, and 4 are reported along with the fluorescence response and affinity of 3 to some metal cations. The origin of the fluorescence from compounds 1 and 4 is investigated using density functional theory and the oscillator strength for each transition is computed. Two deactivation pathways, one of which is only weakly emissive, are identified in 4. In contrast to 4, which is only moderately more emissive than 1 a strong zinc-activated fluorescence response is observed from aqueous solutions of 3.
authors.affiliation: School of Biological and Chemical Sciences, Queen Mary, University of London, Mile End Road, E1 4NS, UK.
authors.forename: Siud Pui
authors.initials: SP
authors.lastname: Man
authors.forename: David M
authors.initials: DM
authors.lastname: Benoit
authors.forename: Ester
authors.initials: E
authors.lastname: Buchaca
authors.forename: Fola
authors.initials: F
authors.lastname: Esan
authors.forename: Majid
authors.initials: M
authors.lastname: Motevalli
authors.forename: John
authors.initials: J
authors.lastname: Wilson
authors.forename: Alice
authors.initials: A
authors.lastname: Sullivan
mesh_terms: D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D015032:Zinc / Q000737:chemistry*
chemical_list: D009942:Organometallic Compounds; D063065:Organophosphonates; D011804:Quinolines; D015032:Zinc