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Issue 24, 2012
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Design and synthesis of triazolyl coumarins as Hg2+ selective fluorescent chemosensors

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Abstract

A series of triazolyl coumarin derivatives L1–L4, with and without spacer groups between the coumarin and the triazole groups, were synthesized as fluorescent sensors to study their binding ability and selectivity toward metal ions. Ligand L3, which contains an acetyl linker between the triazole and the coumarin, exhibited a high selectivity toward Hg2+ in polar protic solvents MeOH–CHCl3 (9 : 1, v/v) with fluorescent enhancement, furthermore, it was found to bind two Hg2+ at a high concentration (>12.5 mM) of Hg(ClO4)2. In contrast, L4, in which position 4 of the triazole unit was replaced by a benzyl group instead of the 4-tert-butylphenoxymethyl group used in L1–L3, showed a binding stoichiometry toward only one Hg2+. On the basis of the fluorescent sensing, IR, and 1H NMR titration results of ligands L1–L4, we proposed that not only the acetyl C[double bond, length as m-dash]O but also the ether group of the 4-tert-butylphenoxymethyl of L3 assisted the triazole nitrogen atoms in the complexation of Hg2+ to form a 1 : 2 complex (L3·(Hg2+)2).

Graphical abstract: Design and synthesis of triazolyl coumarins as Hg2+ selective fluorescent chemosensors

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Publication details

The article was received on 07 Aug 2012, accepted on 25 Sep 2012 and first published on 24 Oct 2012


Article type: Paper
DOI: 10.1039/C2AN36076D
Analyst, 2012,137, 5770-5776

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    Design and synthesis of triazolyl coumarins as Hg2+ selective fluorescent chemosensors

    I. Ho, T. Lai, R. Wu, M. Tsai, C. Wu, G. Lee and W. Chung, Analyst, 2012, 137, 5770
    DOI: 10.1039/C2AN36076D

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