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Multimode selective detection of mercury by chiroptical fluorescent sensors based on methionine/cysteine
Author(s) -
Carney Patrick,
Lopez Steven,
Mickley Amanda,
Grinberg Kirill,
Zhang Wenyao,
Dai Zhaohua
Publication year - 2011
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.21015
Subject(s) - chemistry , fluorescence , metal ions in aqueous solution , chirality (physics) , circular dichroism , fluorophore , photochemistry , quinoline , metal , chelation , amine gas treating , stereochemistry , inorganic chemistry , crystallography , organic chemistry , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
Abstract Two multimode Hg(II) sensors, L‐MethBQA and L‐CysBQA, were obtained by fusing methionine or S ‐methyl cysteine, into a bis‐quinolyl amine‐based chiral podand scaffold. Quinolyl groups serve as the fluorophore and possess nitrogen lone pairs capable of chelating metal ions. On exposure to Hg 2+ or Zn 2+ , these sensors show signal enhancement in fluorescence. However, Cu 2+ quenches their fluorescence in 30:70 acetontrile/water. L‐CysBQA complexes with Hg 2+ , producing an exciton‐coupled circular dichroism spectrum with the opposite sign to the one that is produced by Cu 2+ or Zn 2+ complexation. L‐CysBQA binds Hg 2+ more strongly than Zn 2+ and is shown to differentiate Hg 2+ from other metal ions, such as Zn 2+ , Cu 2+ , Ni 2+ , and Pb 2+ , exceptionally well. The synergistic use of relatively soft sulfur, quinoline‐based chiral ligands and chiroptically enhanced fluorescence detection results in high sensitivity and selectivity for Hg 2+ . Chirality, 2011. © 2011 Wiley‐Liss, Inc.