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Highly Selective Fluorescent Sensors for Hg 2+ and Ag + Based on Bis‐triazole‐Coupled Polyoxyethylenes in MeOH Solution
Author(s) -
Hung HaoChih,
Cheng ChiWen,
Wang YuYun,
Chen YuJen,
Chung WenSheng
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900987
Subject(s) - chemistry , fluorescence , methanol , metal ions in aqueous solution , aqueous solution , pyrene , triazole , selectivity , ether , click chemistry , metal , binding constant , photochemistry , inorganic chemistry , nuclear chemistry , combinatorial chemistry , organic chemistry , binding site , physics , quantum mechanics , biochemistry , catalysis
Fluorescent chemosensors 6 – 9 , with variable length polyoxyethylenes between two triazolylmethyl ether units, have been synthesized under “click” conditions in which the bis‐triazoles and polyoxyethylenes were used as metal‐ion binding sites and the pyrenes as fluorophores. Of the 15 metal ions screened, the fluorescence of chemosensors 6 – 9 in methanol solution was found to be selectively quenched by only Hg 2+ and Ag + . In contrast, the fluorescence of control compound 10 , a [(triazol‐4‐yl)methoxymethyl]pyrene, was quenched by only Hg 2+ . These results imply that the recognition of Hg 2+ does not need the cooperation of two triazole groups. Binding constants for the interactions of 6 – 9 with Ag + increased as the chain length of the polyoxyethylene increased. Finally, a very high selectivity of compound 9 towards Hg 2+ in aqueous methanol solution was observed.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)