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A Pyrene‐Pyrazole‐Based Rotamer Senses Hg 2+ on the Nanomolar Scale
Author(s) -
Naskar Barnali,
Dhara Anamika,
Modak Ritwik,
Maiti Dilip K.,
Prodhan Chandraday,
Chaudhuri Keya,
Requena Alberto,
CerónCarrasco José Pedro,
Goswami Sanchita
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201601780
Subject(s) - conformational isomerism , tautomer , pyrene , chemistry , pyrazole , selectivity , fluorescence , hydrazide , stereochemistry , medicinal chemistry , organic chemistry , molecule , physics , quantum mechanics , catalysis
In this experimental and theoretical study, a new pyrene‐pyrazole based chemosensor, 5‐Methyl‐1H‐pyrazole‐3‐carboxylic acid pyren‐1‐ylm ethylene hydrazide ( MpcphH) , is designed and prepared for selective sensing of Hg 2+ . Photophysical studies, including UV‐vis and fluorescence, showed that MpcphH exhibited high selectivity and sensitivity in response to Hg 2+ with detection limit in the nano molar range. The 1 H and 13 C−NMR spectroscopic techniques are presented to elucidate the coordination modes of MpcphH towards Hg 2+ . The relative stability of the ketoimine/imineol tautomers and the specific rotamer responsible for Hg 2+ coordination are evaluated by means of DFT calculations. Furthermore, MpcphH provides a reliable approach to monitor cellular cytoplasmic Hg 2+ in HepG2 cells.