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Synthesis, Fluorescence, and Two‐Photon Absorption of Bidentate Phosphane Oxide Derivatives: Complexation with Pb 2+ and Cd 2+ Cations
Author(s) -
HaThi MinhHuong,
Penhoat Maël,
Drouin Delphine,
BlanchardDesce Mireille,
Michelet Véronique,
Leray Isabelle
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200800084
Subject(s) - chemistry , fluorescence , absorption (acoustics) , photochemistry , metal ions in aqueous solution , excited state , metal , two photon absorption , ion , sonogashira coupling , absorption spectroscopy , oxide , materials science , palladium , organic chemistry , laser , physics , optics , quantum mechanics , composite material , catalysis , nuclear physics
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 Pb 2+ and Cd 2+ , 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 Cd 2+ sensors combining high affinity for Cd 2+ , 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.