Green Synthesis of Triazole-Based Chemosensors and their Efficacy Towards Mercury Sensing

Author(s): Poonam Rani, Kashmiri Lal*, Vikas D. Ghule, Rahul Shrivastava

Journal Name: Current Analytical Chemistry

Volume 16 , Issue 6 , 2020

Become EABM
Become Reviewer

Graphical Abstract:


Background: The synthesis of small organic molecules based Hg2+ ions receptors have gained considerable attention because it is one of the most prevalent toxic metals which is continuously discharged into the environment by different natural and industrial activities. 1,4-Disubstituted 1,2,3-triazoles have been reported as good chemosensors for the detection of various metal ions including Hg2+ ions.

Methods: The synthesis of 1,2,3-triazoles (4a-4c) was achieved by Cu(I)-catalyzed azide-alkyne cycloaddition, and their binding affinity towards various metal ions and anions were studied by UVVisible titration experiments. The perchlorate salts of metal ions and tetrabutylammonium salts of anions were utilized for the UV-Visible experiments. DFT studies were performed to understand the binding and mechanism on the sensing of 4a toward Hg2+ using the B3LYP/6-311G(d,p) method for 4a and B3LYP/LANL2DZ for 4a-Hg2+ species on the Gaussian 09W program.

Results: The UV-visible experiments indicated that the compounds 4a-4c show a selective response towards Hg2+ ion in UV-Visible spectra, while other ions did not display such changes in the absorption spectra. The binding stoichiometry was evaluated by Job’s plot which indicated the 1:1 binding stoichiometry between receptors (4a-4c) and Hg2+ ion. The detection limit of 4a, 4b and 4c for the Hg2+ ions was found to be 29.1 nM, 3.5 μM and 1.34 μM, respectively.

Conclusion: Some 1,2,3-triazole derivatives were synthesized (4a-4c) exhibiting high selectively and sensitivity towards Hg2+ ions in preference to other ions. Compound 4a has a low detection limit of 29.1 nM and the binding constant of 2.3×106 M-1. Similarly, 4b and 4c also showed selective sensing towards Hg2+ ions in the μM range. The observed experimental results were corroborated by density functional theory (DFT) calculations.

Keywords: 1, 2, 3-Triazole, chemosensors, cycloaddition, mercury ion, UV-Visible spectra, absorption spectra.

Mercury. NIEHS. Archived from the original on 19 November 2016, 2016.
Bose-O’Reilly, S.; McCarty, K.M.; Steckling, N.; Lettmeier, B. Mercury exposure and children’s health. Curr. Probl. Pediatr. Adolesc. Health Care, 2010, 40(8), 186-215. [ ]. [PMID: 20816346].
Miller, J.R.; Rowland, J.; Lechler, P.J.; Desilets, M.; Hsu, L.C. Dispersal of mercury-contaminated sediments by geomorphic processes, Sixmile Canyon, Nevada, USA: Implications to site characterization and remediation of fluvial environments. Water Air Soil Pollut., 1996, 86, 373-388.
Rama, I.; Selvameena, R. Synthesis, structure analysis, antibacterial and in vitro anti-cancer activity of new Schiff base and its copper complex derived from sulfamethoxazole. J. Chem. Sci., 2015, 127, 671-678..
Cherian, M.G.; Hursh, J.B.; Clarkson, T.W.; Allen, J. Radioactive mercury distribution in biological fluids and excretion in human subjects after inhalation of mercury vapor. Arch. Environ. Health, 1978, 33(3), 109-114. [ ]. [PMID: 686833].
Bernhoft, R.A.J. Mercury toxicity and treatment: A review of the literature. J. Environ. Public Health, 2012, 2012, 460508 [ ]. [PMID: 22235210].
Gao, Z.; Liu, Z.; Chen, X.; Lai, Z.; Huang, Z. Carbon dots-based fluorescent probe for trace Hg2+ detection in water sample. Sens.Actuat. B Chem., 2016, 222, 965-971..
Ayesh, A.; Karam, Z.; Awwad, F.; Meetani, M.A. Conductometric graphene sensors decorated with nanoclusters for selective detection of Hg2+ traces in water. Sens. Actuat. B Chem., 2015, 221, 201-206.
Hsu, I.H.; Hsu, T.C.; Sun, Y.C. Gold-nanoparticle-based graphite furnace atomic absorption spectrometry amplification and magnetic separation method for sensitive detection of mercuric ions. Biosens. Bioelectron., 2011, 26(11), 4605-4609. [ ]. [PMID: 21605967].
Huang, D.; Niu, C.; Wang, X.; Lv, X.; Zeng, G. “Turn-on” fluorescent sensor for Hg2+ based on single-stranded DNA functionalized Mn:CdS/ZnS quantum dots and gold nanoparticles by time-gated mode. Anal. Chem., 2013, 85(2), 1164-1170. [ ]. [PMID: 23256544].
Du, J.; Hu, M.; Fan, J.; Peng, X. Fluorescent chemodosimeters using “mild” chemical events for the detection of small anions and cations in biological and environmental media. Chem. Soc. Rev., 2012, 41(12), 4511-4535. [ ]. [PMID: 22535221].
Kim, H.N.; Ren, W.X.; Kim, J.S.; Yoon, J. Fluorescent and colorimetric sensors for detection of lead, cadmium, and mercury ions. Chem. Soc. Rev., 2012, 41(8), 3210-3244. [ ]. [PMID: 22184584].
Huang, P.; Liu, B.; Jin, W.; Wu, F.; Wan, Y. Colorimetric detection of Cd2+ using 1-amino-2-naphthol-4-sulfonic acid functionalized silver nanoparticles. J. Nanopart. Res., 2016, 18, 327-336..
Wan, J.; Zhang, K.; Li, C.; Li, Y.; Niu, S. A novel fluorescent chemosensor based on a rhodamine 6G derivative for the detection of Pb2+ ion. Sens. Actuat. B Chem., 2017, 246, 696-702..
Deshpande, S.S.; Jachak, M.A.; Khopkar, S.S.; Shankarling, G.S. A simple substituted spiropyran acting as a photo reversible switch for the detection of lead (Pb2+) ions. Sens. Actuators B Chem., 2018, 258, 648-656..
Shaily; Kumar, A.; Parveen, I.; Ahmed, N. Highly selective and sensitive coumarin-triazole-based fluorometric ‘turn-off’ sensor for detection of Pb2+ ions. Luminescence, 2018, 33(4), 713-721. [ ]. [PMID: 29498808].
Anjul, K.; Pramod, S.P. Steroidal 1,2,3-triazole-based sensors for Hg2+ ion and their logic gate behavior Tetrahedron Lett., 2009, 50, 5842-5845.
Arasappan, H.; Thangamuthu, M.D. Design and synthesis of sugar-triazole low molecular weight gels as mercury ion sensor. New J. Chem., 2013, 37, 2419-2425.
Lal, K.; Yadav, P.; Kumar, A. Synthesis, characterization and antimicrobial activity of 4-((1-benzyl/phenyl-1H-1, 2, 3-triazol-4-yl)methoxy) benzaldehyde analogues Med. Chem. Res., 2016, 25(4), 644-652..
Devatha, P.N.; Maciej, P.; Shunsuke, C.; Tao, G.; Weixian, X.; Christopher, R.F.; Christopher, N.B. The Thiol-Michael addition Click Reaction: A powerful and widely used tool in materials chemistry. Chem. Mater., 2014, 26(1), 724-744..
Byrne, J.P.; Kitchen, J.A.; Gunnlaugsson, T. The btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] binding motif: A new versatile terdentate ligand for supramolecular and coordination chemistry. Chem. Soc. Rev., 2014, 43(15), 5302-5325. [ ]. [PMID: 24871484].
Debia, N.P.; Saraiva, M.T.; Martins, B.S.; Beal, R.; Gonçalves, P.F.B.; Rodembusch, F.S.; Alves, D.; Lüdtke, D.S. Goncalves; Fabiano, S. R.; Diego, A.; Diogo S. L. Synthesis of amino acid-derived 1,2,3-triazoles: development of a nontrivial fluorescent sensor in solution for the enantioselective sensing of a carbohydrate and bovine serum albumin interaction. J. Org. Chem., 2018, 83(3), 1348-1357. [ ]. [PMID: 29313350].
Hemamalini, A.; Das, T.M. Design and synthesis of sugar-triazole low molecular weight gels as mercury ion sensor. New J. Chem., 2013, 37, 2419-2425..
Mandal, D.; Thakur, A.; Ghosh, S. A triazole tethered triferrocene derivative as a selective chemosensor for mercury(II) in aqueous environment. Polyhedron, 2013, 52, 1109..
Lal, K.; Rani, P.; Shrivastava, R. Sensing and quantification of Hg2+ ions based on aggregation of carbamate linked-triazole stabilized silver nanoparticles. Chem. Biol. Interface, 2019, 9, 127-135.
Hu, J.; Zhang, M.; Yu, L.B.; Ju, Y. Synthesis and binding ability of 1,2,3-triazole-based triterpenoid receptors for recognition of Hg(2+) ion. Bioorg. Med. Chem. Lett., 2010, 20(15), 4342-4345. [ ]. [PMID: 20609584].
Dipendu, M.; Arunabha, T.; Sundargopal, G. A triazole tethered triferrocene derivative as a selective chemosensor for mercury(II) in aqueous environment. Polyhedron, 2013, 52, 1109-1117..
Roop, S.S.; Rakesh, K.G.; Rajendra, P.P.; Arvind, M.; Daya, S.P. Triazole-appended BODIPY-piperazine conjugates and their efficacy toward mercury sensing. New J. Chem., 2015, 39, 2233-2239..
Khan, B.; Hameed, A.; Minhaz, A.; Shah, M.R. Synthesis and characterisation of calix[4]arene based bis(triazole)-bis(hexahydro-[quinoline): Probing highly selective fluorescence quenching towards mercury (Hg2+) analyte. J. Hazard. Mater., 2018, 347, 349-358. [ ]. [PMID: 29335217].
Xu, S.; Zhuang, X.; Pan, X.; Zhang, Z.; Duan, L.; Liu, Y.; Zhang, L.; Ren, X.; Ding, K. 1-Phenyl-4-benzoyl-1H-1,2,3-triazoles as orally bioavailable transcriptional function suppressors of estrogen-related receptor α. J. Med. Chem., 2013, 56(11), 4631-4640. [ ]. [PMID: 23656512].
Chavan, P.V.; Pandit, K.S.; Desai, U.V.; Kulkarni, M.A.; Wadgaonkar, P.P. Cellulose supported cuprous iodide nanoparticles (Cell-CuI NPs): A new heterogeneous and recyclable catalyst for the one pot synthesis of 1,4-disubstituted 1,2,3-triazoles in water. RSC Adv 2014, 4, 42137-42146..
Xiaofeng, Y.; Gege, Z.; Yexin, L.; Zheng, L.; Xiaoqian, G.; Bin, G.; Guangyou, Z.; Yu, C.; Guoxin, S. Colorimetric and fluorogenic signalling of fluoride ions by diketopyrrolopyrrole-based chemosensor. RSC Adv., 2015, 5, 22455-22462..
Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E. Gaussian 09,revision E.01; Gaussian, Inc.: Wallingford, CT, 2013.

Rights & PermissionsPrintExport Cite as

Article Details

Year: 2020
Page: [738 - 743]
Pages: 6
DOI: 10.2174/1573411015666191010122744
Price: $65

Article Metrics

PDF: 25