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Synthesis and sensing properties of 1,1′-disubstituted unsymmetrical ferrocene-triazole derivatives: A multichannel probe for Hg(ii) ion
Bijan Mondal, Joseph Ponniah S,
Published in
2013
Volume: 3
   
Issue: 40
Pages: 18614 - 18625
Abstract
Triazole-based unsymmetrically 1,1′-disubstituted ferrocene derivatives 4 and 5 have been synthesized using "click chemistry" with sequential functionalization at the cyclopentadienyl rings. The cation complexation properties of these ferrocene derivatives have been studied using electrochemical and spectroscopic techniques. The exceptional structural features present in these ligands are the presence of one cholesterol moiety, connected to the 1-position of the ferrocene center through a 1,2,3-triazole ring, and a fluorescent moiety, linked to the 1′-position of such a core through another triazole-ether linkage. Both the receptors experience perturbation of the CV in the presence of Hg2+ with a change of electrochemical potential (the large anodic shift ΔE1/2 = 129 mV for 4 and ΔE1/2 = 140 mV for 5). The changes in the absorption spectra are accompanied by the appearance of a new high energy (HE) peak at ca. 206 nm for 4 and 202 nm for 5 (4: ε = 3123 × 10 2 M-1 cm-1, 5: ε = 3140 × 10 2 M-1 cm-1) in the presence of Hg2+ ion. In addition, receptors 4 and 5 show colorimetric response and act as a selective "turn off" fluorescent receptor for Hg2+ and Cu2+ ions. On the basis of the 1H NMR titration, ESI-MS and DFT study, probable binding modes of 1,1′-disubstituted ferrocene derivatives 4 and 5 with Hg2+ have been proposed. © 2013 The Royal Society of Chemistry.
About the journal
JournalRSC Advances
ISSN20462069
Open AccessNo
Concepts (13)
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    COMPLEXATION PROPERTIES
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    CYCLOPENTADIENYL RINGS
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    Electrochemical potential
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    FERROCENE CENTER
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    Ferrocene derivative
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    SEQUENTIAL FUNCTIONALIZATION
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    Spectroscopic technique
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    Structural feature
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    Binding energy
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    Fluorescence
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    Ions
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    Nitrogen compounds
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    Organometallics