Aqueous Ln(III) luminescence agents derived from a tasty precursor.

Inorganic Chemistry
Christoph J JocherKenneth N Raymond

Abstract

The synthesis, characterization, and photophysical properties are reported for several Ln(III) complexes of a tetradentate chelate, 5LIO-MAM, derived from the common flavor enhancer "maltol". Eu(III), Yb(III), and Nd(III) form stable ML2 complexes in aqueous solution that emit in the red or near-infrared (NIR) upon excitation at ca. 330 nm. The synthesis, aqueous stability, and photophysical properties are reported for a novel tetradentate ligand derived from maltol, a commonly used flavor enhancer. In aqueous solution, this chelate forms stable complexes with Ln(III) cations, and sensitized emission was observed from Eu(III), Yb(III), and Nd(III). A comparison with recently reported and structurally analogous ligands reveals a slightly higher basicity but lower complex stability with Eu(III) [pEu = 14.7(1)]. A very poor metal-centered quantum yield with Eu(III) was observed (Phi(tot) = 0.04%), which can be rationalized by the similar energy of the ligand triplet state and the Eu(III) (5)D0 emissive level. Instead, sensitized emission from the Yb(III) and Nd(III) cations was observed, which emit in the NIR.

References

May 20, 2004·Bioorganic & Medicinal Chemistry Letters·Paola PaceVincenzo Summa
Jan 20, 2005·Bioconjugate Chemistry·Kenneth N Raymond, Valérie C Pierre
Feb 16, 2006·Journal of the American Chemical Society·David T PuertaSeth M Cohen
Aug 17, 2006·Journal of the American Chemical Society·Evan G MooreKenneth N Raymond
Jan 4, 2007·Journal of the American Chemical Society·Stéphane PetoudKenneth N Raymond
Oct 5, 2007·Inorganic Chemistry·Christoph J JocherKenneth N Raymond
Mar 4, 2008·Inorganic Chemistry·Evan G MooreKenneth N Raymond

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Citations

Apr 5, 2012·Inorganic Chemistry·Christine DoffekMichael Seitz
Sep 3, 2009·Inorganic Chemistry·Anthony D'AléoKenneth N Raymond
May 15, 2009·Dalton Transactions : an International Journal of Inorganic Chemistry·Stephen FaulknerDaniel Sykes
Dec 22, 2009·Chemical Society Reviews·Svetlana V Eliseeva, Jean-Claude G Bünzli
Jan 9, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Ana C MendonçaM Amélia Santos
Sep 22, 2009·The Journal of Physical Chemistry. a·Masahisa OsawaShuichi Osanai
Apr 6, 2017·Environmental Science & Technology·Sarah M HarrisValérie C Pierre

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