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Synthesis of triazole linked fluorescent amino acid and carbohydrate bio-conjugates: A highly sensitive and skeleton selective multi-responsive chemosensor for Cu(ii) and Pb(ii)/Hg(ii) ions
Bijan Mondal,
Published in
2014
Volume: 4
   
Issue: 4
Pages: 1918 - 1928
Abstract
A set of triazole-based chromogenic and fluorescent chemosensors with amino acid/carbohydrate-fluorophore conjugates have been designed and synthesized. The metal cation-sensing properties of glycine-anthracene, C24H 24O4N4 (3), glycine-pyrene C26H 24O4N4 (4), glucose-anthracene, C 32H33O10N3 (5) and glucose-pyrene, C34H33O10N3 (6) bio-conjugates have been studied systematically. The significant changes in their absorption spectra are accompanied by a strong color change from light yellow to brown for 3 and 4 and colorless to greenish blue for 5 and 6. Receptors 3 and 4 have potential in the "naked eye" detection of Cu2+ and 5 and 6 for Pb 2+/Hg2+ ion. The receptors 3 and 4 show fluorescence diminution following Cu2+ coordination within the limit of detection at 0.89 parts per billion (ppb) and this is unprecedented, whereas the receptors 5 and 6 present drastic fluorescence quenching upon addition of Hg2+ and Pb2+ within the limit of detection at 4 and 2 ppb respectively. Interestingly, their fluorescence and colorimetric responses are preserved in the presence of water that can be used for the selective colorimetric detection of these ions in aqueous environments. Along with the spectroscopic data, combined 1H NMR titration of the complexes and the DFT studies suggest the proposed coordination modes. © 2014 The Royal Society of Chemistry.
About the journal
JournalRSC Advances
ISSN20462069
Open AccessNo
Concepts (19)
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    Aqueous environment
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    Colorimetric detection
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    Coordination modes
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    Fluorescence quenching
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    FLUORESCENT CHEMOSENSORS
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    Limit of detection
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    Presence of water
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    Spectroscopic data
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    Amino acids
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    Anthracene
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    Colorimetry
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    Coordination reactions
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    Glucose
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    Ions
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    Lead
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    Nitrogen compounds
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    Physiology
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    Pyrene
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    Fluorescence