Synthesis, fluorescence, and two-photon absorption of bidentate phosphane oxide derivatives: complexation with pb(2+) and cd(2+) cations.
A series of fluorescent phosphane oxide derivatives based on diphenylphosphanoethane (DPPE) and diphenylphosphanomethane (DPPM) skeletons has been prepared by means of Grignard reactions and Sonogashira cross-couplings. The photophysical properties and the linear and nonlinear spectra of these compounds have been investigated. An edge-to-face conformation resulting in the formation of an excimer was confirmed by fluorescence lifetime measurements of these multichromophoric derivatives. Upon complexation with heavy metal ions such as Pb2+ and Cd2+, a red shift of the one- and two-photon excitation spectra was observed in the absorption and emission spectra. Furthermore, enhancement of the electron-withdrawing character of the phosphane oxide resulted in a significant enhancement of the two-photon absorption cross-section, leading to the first biphotonic Cd2+ sensors combining high affinity for Cd2+, large two-photon absorption cross-sections, and significant enhancement of the two-photon excited fluorescence in the presence of the cation. Such derivatives are highly promising for incorporation into devices for the detection of heavy metal ions in water and effluents.
Ha-Thi
Minh-Huong
MH
Laboratoire de Photophysique et Photochimie, Supramoléculaires et Macromoléculaires (CNRS UMR 8531), ENS-Cachan, 61 avenue du Président Wilson, 94235 Cachan Cedex (France).
Penhoat
Maël
M
Drouin
Delphine
D
Blanchard-Desce
Mireille
M
Michelet
Véronique
V
Leray
Isabelle
I
D002104:Cadmium / Q000737:chemistry*; D002413:Cations, Divalent; D004583:Electrons; D005456:Fluorescent Dyes / Q000138:chemical synthesis*; D007854:Lead / Q000737:chemistry*; D008024:Ligands; D008956:Models, Chemical; D009942:Organometallic Compounds / Q000737:chemistry*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis*; D010720:Phosphines / Q000737:chemistry*; D017785:Photons; D013050:Spectrometry, Fluorescence / Q000379:methods*
D002413:Cations, Divalent; D005456:Fluorescent Dyes; D008024:Ligands; D009942:Organometallic Compounds; D009943:Organophosphorus Compounds; D010720:Phosphines; D002104:Cadmium; D007854:Lead