Development of a Benzimidazole‐Based Fluorescent Probe for the Sensitive and Selective Detection of Mercury(II) Ions

Development of a Benzimidazole‐Based Fluorescent Probe for the Sensitive and Selective Detection of Mercury(II) Ions S. Dhanapal Department of Chemistry Karpagam Academy of Higher Education Coimbatore 641 021 India Centre for Material Chemistry Karpagam Academy of Higher Education (Deemed to be University) Coimbatore 641 021 India R. Veerasamy Department of Chemistry Karpagam Academy of Higher Education Coimbatore 641 021 India Department of Chemistry K.S.R. College of Engineering Tiruchengode 637 215 India N. S. Sangeetha Department of Chemistry Anna Adarsh College for Women Chennai 600040 India F. Riyazur Rahman Department of Chemistry Karpagam Academy of Higher Education Coimbatore 641 021 India A. Kosiha Department of Chemistry School of Basic Sciences Vels Institute of Science Technology & Advanced Studies (VISTAS) (Deemed to be University) Chennai 600 117 India G. Kalaiarasi Department of Chemistry Karpagam Academy of Higher Education Coimbatore 641 021 India Centre for Material Chemistry Karpagam Academy of Higher Education (Deemed to be University) Coimbatore 641 021 India Abstract

In this work, we have synthesized and characterized a new benzimidazole appended Schiffbase‐based fluorescent chemosensor 2‐((1H‐benzo[d]imidazol‐2‐yl)thio)‐N‐(4‐(2‐(2‐(2‐hydroxy‐3‐methoxybenzylidene)hydrazinyl)phenyl)acetamide ( MBIA ) for sensitive and selective detection of Hg 2+ ions. In the presence of Hg 2+ ions, MBIA shows an immediate turn off response of blue fluorescence and a color change from colorless to pale yellow in DMF‐Water (1:4 v/v) medium. MBIA forms a strong complex with Hg 2+ having binding constant 2.19 ± 0.55 × 10 7 M −1 . From the results of Job's plot, NMR titration, Mass spectrometric studies and DFT studies we reveal the stoichiometry of MBIA ‐ Hg 2+ system is 2:1. The Limit of detection (LOD) for MBIA towards Hg 2+ ions is 2.80 × 10 −7 M. The practical utility of MBIA in real sample analysis is examined by spiking Hg 2+ in water samples collected from various sources such as tap water and drinking water. Furthermore, MBIA and its Hg 2+ complex ( MBIA ‐ Hg 2+ ) possesses significant anticancer activity against HeLa (Human cervical cancer cell line) and A549 (Human lung adenocarcinoma cell line) cancer cell lines with encouraging outcomes. This dual functionality such as sensing activity and anticancer nature of this probe makes it as the stand alone work in the fields of both environmental and biological chemistry.
03 31 2025 04 2025 e202405471 10.1002/slct.202405471 2 10.1002/crossmark_policy chemistry-europe.onlinelibrary.wiley.com true 2024-11-21 2025-03-17 2025-03-31 Karpagam Academy of Higher Education https://doi.org/10.13039/100018248 KAHE/R‐Acad/A1/SeedMoney/009,Dt1stNovember2023. http://onlinelibrary.wiley.com/termsAndConditions#vor 10.1002/slct.202405471 https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/slct.202405471 10.3390/ijms251810127 10.12692/ijb/12.4.223-240 Spectrochim. Acta A Mol. Biomol. Spectrosc. Yilmaz B. 118904 245 2020 10.1016/j.saa.2020.118904 10.3390/molecules26195773 10.1007/s10895-023-03455-1 10.1039/D0AY00913J IntechOpen eBooks. Yahya M. 2022 10.1016/j.saa.2021.119610 10.1007/s10895-018-02342-4 10.1007/s10895-021-02818-w IntechOpen eBooks Basheer S. M. 2023 10.1039/D1MA01175H 10.3390/molecules28196960 10.1016/j.snb.2020.129418 10.1016/j.saa.2020.118784 10.1016/j.molliq.2021.116122 10.1016/j.saa.2020.118657 J. Fluoresc. Jaswal A. 1 2024 10.3390/molecules26196060 Int. J. Environ. Sci. Technol. Moukadiri H. 3407 21 2023 10.1007/s13762-023-05275-z Sci. Total Environ. Rasheed T. 476 615 2017 10.1016/j.scitotenv.2017.09.126 10.1080/10408347.2023.2186695 10.1016/j.molstruc.2018.01.004 10.1016/j.aca.2022.339824 10.1016/j.microc.2022.107991 J. Lumin Guan W. L. 118722 244 2021 10.1016/j.jlumin.2021.118722 J. Photochem. Photobiol. A Chem. Bakir E. M. 113569 422 2021 10.1016/j.jphotochem.2021.113569 Eur. Polym. J. Ozmen P. 110922 162 2021 10.1016/j.eurpolymj.2021.110922 10.1016/j.seppur.2022.121471 Spectrochim. Acta A Mol. Biomol. Spectrosc. Musikavanhu B. 120338 264 2021 10.1016/j.saa.2021.120338 10.1039/D3SD00346A Inorg. Chim. Acta. Mohan B. 63 486 2018 10.1016/j.ica.2018.10.022 10.1016/j.scitotenv.2022.157242 10.1039/C8DT05097J 10.1016/j.saa.2020.118610 10.1016/j.jphotochem.2018.01.017 J. Photochem. Photobiol. A Chem. Bayindir S. 235 372 2018 10.1016/j.jphotochem.2018.12.021 10.1186/s43094-020-00048-8 BMC Chem. Yavuz S. C. 146 18 2024 10.1186/s13065-024-01241-z 10.2174/1871520622666220429134818 ChemistrySelect Choudhary A. e20220491 8 2023 10.1002/slct.202204910 10.3390/nutraceuticals4040030 10.1016/j.snb.2013.12.044 M. J.Frisch G. W.Trucks H. B.Schlegel G. E.Scuseria M. A.Robb J. R.Cheeseman J. A.Montgomery T.Vreven K. N.Kudin J. C.Burant J. M.Millam S. S.Iyengar J.Tomasi V.Barone B.Mennucci M.Cossi G.Scalmani N.Rega G. A.Petersson H.Nakatsuji M.Hada M.Ehara K.Toyota R.Fukuda J.Hasegawa M.Ishida T.Nakajima Y.Honda O.Kitao H.Nakai M.Klene X.Li J. E.Knox H. P.Hratchian J. B.Cross V.Bakken C.Adamo J.Jaramillo R.Gomperts R. E.Stratmann O.Yazyev A. J.Austin R.Cammi C.Pomelli J. W.Ochterski P. Y.Ayala K.Morokuma G. A.Voth P.Salvador J. J.Dannenberg V. G.Zakrzewski S.Dapprich A. D.Daniels M. C.Strain O.Farkas D. K.Malick A. D.Rabuck K.Raghavachari J. B.Foresman J. V.Ortiz Q.Cui A. G.Baboul S.Clifford J.Cioslowski B. B.Stefanov G.Liu A.Liashenko P.Piskorz I.Komaromi R. L.Martin D. J.Fox T.Keith M. A.Al‐Laham C. Y.Peng A.Nanayakkara M.Challacombe P. M. W.Gill B.Johnson W.Chen M. W.Wong C.Gonzalez J. A.Pople Gaussian 03 Revision C.02 Gaussian Inc. Wallingford CT2004. Gauss View Molecular Visualization Program. User Manual Frisch A. 2001 10.1007/s13596-020-00531-w 10.1016/j.jphotochem.2019.111947 10.1016/j.jphotochem.2023.114871 10.1016/j.ica.2017.09.051 10.1021/acsomega.1c07193 10.1039/c1dt11838b 10.1016/j.saa.2021.119776 10.1002/jccs.201900188 10.1016/j.talanta.2016.10.004 10.1007/s10895-020-02563-6 10.1016/j.snb.2018.12.003 10.1002/slct.201903109 10.1039/C5RA21474B 10.1016/j.dyepig.2016.01.008 10.1016/j.saa.2019.03.106 10.1039/c2ra21202a 10.5012/bkcs.2010.31.5.1371 10.1016/j.jphotochem.2022.114491 10.1016/j.molliq.2021.116122 10.1002/slct.202000652 10.1016/j.inoche.2016.10.017 10.1016/j.molstruc.2020.129701 10.1016/j.saa.2016.11.022 10.1002/jcc.25825 Inorganica Chim. Acta. Mallela R. 66 469 2017 10.1016/j.ica.2017.08.042 10.1002/jccs.202100135 10.3390/cells13221838 10.1016/j.mtcomm.2018.02.024 10.1016/j.talo.2024.100353 10.1016/j.molliq.2023.122442