Copyright (c) 2025 Sanket Kumar Chakravarti, Vibha Sharma, Abhay Nanda Srivastva, Som Shankar Dubey, Netra Pal Singh

This work is licensed under a Creative Commons Attribution 4.0 International License.
Carboxamide-Based Probe for Highly Selective Detection of Copper Ions: Synthesis, Spectroscopic Analysis, Theoretical Investigations and Catalytic Activity
Corresponding Author(s) : Netra Pal Singh
Asian Journal of Chemistry,
Vol. 37 No. 9 (2025): Vol 37 Issue 9, 2025
Abstract
A carboxamide based fluorescent probe N2,N6-bis(5-(p-tolyl)thiazol-2-yl)pyridine-2,6-dicarboxamide was synthesized by the condensation reaction between pyridine-2,6-dicarboxylic and amino derivative of thiazole and characterized by FT-IR spectroscopy, 1H NMR, 13C NMR, UV-vis spectroscopy and LC-MS spectral studies. Absorption and fluorescence titrations were used to study the fluorescent. The probe exhibits high selectivity and sensitivity towards Cu2+ ions over a spectrum of metal ions (Cu2+, Co2+, Ni2+, Hg2+, Cr3+, Al3+, Fe2+, Sn2+ and Pb2+). Using Job’s plot measurements, the binding stoichiometry mode of the probe with the Cu2+ ion was estimated to be 2:1. The Benesi-Hildebrand equation yielded a stability constant value of 8.252 × 107 M–2 for the fluorescent probe. It was found that the fluorescent probe’s limit of detection (LOD) for the Cu2+ ion was 0.0242 µM. DFT analyses have also been performed to support the sensing technique. The Cu(II) complex's catalytic activity was assessed using the one-pot azide–alkyne cycloaddition click reaction in water without the use of any supplementary agents.
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References
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E. Senkuytu and E.T. Eçik, Spectrochim. Acta A Mol. Biomol. Spectrosc., 173, 863 (2017); https://doi.org/10.1016/j.saa.2016.10.052
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S. Yang, W. Fan, D. Wang, Z. Gong and M. Fan, Anal. Methods, 11, 3829 (2019); https://doi.org/10.1039/C9AY00709A
X. Xie, X. Chen, B. Li and L. Zhang, Dyes Pigments, 98, 422 (2013); https://doi.org/10.1016/j.dyepig.2013.03.022
V. Desai and S.G. Kaler, Am. J. Clin. Nutr., 88, 855S (2008); https://doi.org/10.1093/ajcn/88.3.855S
K. Ghosh and D. Kar, J. Incl. Phenom. Macrocycl. Chem., 77, 67 (2012); https://doi.org/10.1007/s10847-012-0217-6
Y. Zheng, K.M. Gattas-Asfura, V. Konka and R.M. Leblanc, Chem. Commun., 2350 (2002); https://doi.org/10.1039/B208012E
M. Saleem, M. Rafiq, M. Hanif, M.A. Shaheen and S.-Y. Seo, J. Fluoresc. 28, 97 (2018); https://doi.org/10.1007/s10895-017-2178-z
S. Chowdhury, B. Rooj, A. Dutta and U. Mandal, J. Fluoresc., 28, 999 (2018); https://doi.org/10.1007/s10895-018-2263-y
K.P. Carter, A.M. Young and A.E. Palmer, Chem. Rev., 114, 4564 (2014); https://doi.org/10.1021/cr400546e
E.V. Antina, N.A. Bumagina, A.I. V’Yugin and A.V. Solomonov, Dyes Pigments, 136, 368 (2017); https://doi.org/10.1016/j.dyepig.2016.08.070
A. Torrado, G.K. Walkup and B. Imperiali, J. Am. Chem. Soc., 120, 609 (1998); https://doi.org/10.1021/ja973357k
G. Klein, D. Kaufmann, S. Schürch and J.-L. Reymond, Chem. Commun. 561 (2001); https://doi.org/10.1039/B100535I
M. Boiocchi, L. Fabbrizzi, M. Licchelli, D. Sacchi, M. V´azquez and C. Zampa, Chem. Commun., 1812 (2003); https://doi.org/10.1039/B305456J
Y. Zheng, J. Orbulescu, X. Ji, F.M. Andreopoulos, S.M. Pham and R.M. Leblanc, J. Am. Chem. Soc., 125, 2680 (2003); https://doi.org/10.1021/ja0293610
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S.H. Kim, J.S. Kim, S.M. Park and S.-K. Chang, Org. Lett., 8, 371 (2006); https://doi.org/10.1021/ol052282j
T.C Harrop and P.K. Mascharak, Acc. Chem. Res., 37, 253 (2004); https://doi.org/10.1021/ar0301532
A. Rajput and R. Mukherjee, Coord. Chem. Rev., 257, 350 (2013); https://doi.org/10.1016/j.ccr.2012.03.024
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P.J. Donoghue, J. Tehranchi, C.J. Cramer, R. Sarangi. E.I. Solomon and W.B. Tolman, J. Am. Chem. Soc., 133, 17602 (2011); https://doi.org/10.1021/ja207882h
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F. Neese, Wiley Interdiscip. Rev. Comput. Mol. Sci., 2, 73 (2012); https://doi.org/10.1002/wcms.81
M.D. Hanwell, D.E. Curtis, D.C. Lonie, T. Vandermeersch, E. Zurek and G.R. Hutchison, J. Cheminform., 4, 2 (2012); https://doi.org/10.1186/1758-2946-4-17
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S. Sinha, R. R. Koner, S. Kumar, J. Mathew, P.V. Monisha, I. Kazia and S. Ghosh, RSC. Adv., 3, 345 (2013); https://doi.org/10.1039/C2RA21967K
G. Dong, K. Duan, Q. Zhang and Z. Liu, Inorg. Chim. Acta, 487, 322 (2019); https://doi.org/10.1016/j.ica.2018.12.036
H. Wang, D. Wang, Q. Wang, X. Li and C.A. Schalley, Org. Biomol. Chem., 8, 1017 (2010); https://doi.org/10.1039/B921342B
L.M. Liu and Z.Y. Yang, Inorg. Chim. Acta, 469, 588 (2018); https://doi.org/10.1016/j.molstruc.2022.134329
S. Zehra, R.A Khan, A. Alsalme and S. Tabassum, J. Fluorosc., 29 1029 (2019); https://doi.org/10.1039/C9RA06356K
M. Asadi and M.S. Khah, J. Iran. Chem. Soc., 7, 875 (2010); https://doi.org/10.1007/BF03246082
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