Abstract
Development of fluorescent sensors with large Stokes shift for selective detection of heavy metals is of great importance. A novel fluorescent probe with extremely large Stokes shift (212 nm) was synthesized for selective and simultaneous detection of Hg2+ and Ag+ ions. The deep yellow probe turned colorless or pale yellow after addition of Hg2+ or Ag+. The new probe could be utilized for absorption spectral detection of Hg2+ and Ag+ both in ethanol and aqueous solution. Addition of Hg2+ and Ag+ ions caused significant decrease in the fluorescence intensity of the new probe and the selective recognition of Hg2+ and Ag+ was not interfered by common competitive metal ions including Li+, Na+, K+, Cu2+, Fe2+, Zn2+, Co2+, Ni2+, Mn2+, Sr2+, Ca2+, Mg2+, Al3+, Cr3+ and Fe3+. The detection limit for Hg2+ and Ag+ was calculated to be 4.68 μM and 4.29 μM, respectively. Application of the new probe for quantitative determination of Hg2+ and Ag+ concentrations in real water samples was accomplished.
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References
Ebrahimi-znajafabadi H, Pasdaran A, Bezebjani RR, Bozorgzadeh E (2019) Determination of toxic heavy matals in rice samples using ultrasound assisted emulsification microextraction combined with inductively coupled plasma optical emission spectroscopy. Food Chem 289:26–32. https://doi.org/10.1016/j.foodchem.2019.03.046
Hutton LA, O’Neil GD, Read TL, Ayres ZJ, Newton ME, Macpherson JV (2014) Electrochemical x-ray fluorescence spectroscopy for trace heavy metal analysis: Enhanced x-ray fluorescence detection capabilities by four orders of magnitude. Anal Chem 86:4566–4572. https://doi.org/10.1021/ac500608d
Safari Y, Karimaei M, Sharafi K, Arfaeinia H, Moradi M, Fattahi N (2018) Persistent sample circulation microextraction combined with graphite furnace atomic absorption spectroscopy for trace determination of heavy metals in fish species marketed in Kermanshah, Iran, and human health risk assessment. J Sci Food Agric 98:2915–2924. https://doi.org/10.1002/jsfa.8786
Hanhauser E, Bono Jr MS, Vaishnav C, Hart AJ, Karnik R (2020) Solid-phase extraction, preservation, storage, transport, and analysis of trace contaminants for water quality monitoring of heavy metals. Environ Sci Technol 54:2646−2657. https://doi.org/10.1021/acs.est.9b04695
Bings NH, Bogaerts A, Broekaert JAC (2010) Atomic spectroscopy: a review. Anal Chem 82:4653–4681. https://doi.org/10.1021/ac1010469
Ding Q, Li C, Wang H, Xu C, Kuang H (2021) Electrochemical detection of heavy metal ions in water. Chem Commun 57:7215–7231. https://doi.org/10.1039/d1cc00983d
Tian C, Zhao L, Zhu J, Zhang S (2022) Simultaneous detection of trace Hg2+ and Ag+ by SERS Aptasensor based on a novel cascade amplification in environmental water. Chem Eng J 435:133879. https://doi.org/10.1016/j.cej.2021.133879
Liu C, Ye Z, Wei X, Mao S (2022) Recent advances in field-effect transistor sensing strategies for fast and highly efficient analysis of heavy metal ions. Electrochem Sci Adv 2:e2100137. https://doi.org/10.1002/elsa.202100137
Rurack K, Kollmannsberger M, Resch-Genger U, Daub J (2000) A selective and sensitive fluoroionophore for HgII, AgI, and CuII with virtually decoupled fluorophore and receptor units. J Am Chem Soc 122:968−969. https://doi.org/10.1021/ja9926630a
Hien NK, Bao NC, Nhung NTA, Trung NT, Nam PC, Duong T, Kim JS, Quang DT (2015) A highly sensitive fluorescent chemosensor for simultaneous determination of Ag(I), Hg(II), and Cu(II) ions: Design, synthesis, characterization and application. Dyes Pigm 116:89−96. https://doi.org/10.1016/j.dyepig.2015.01.014
Zhang S, Wu X, Niu Q, Guo Z, Li T, Liu H (2017) Highly selective and sensitive colorimetric and fluorescent chemosensor for rapid detection of Ag+, Cu2+ and Hg2+ based on a simple Schiff base. J Fluoresc 27 729−737. https://doi.org/10.1007/s10895-016-2005-y
Ribeiro DSM, Castro RC, Páscoa RNMJ, Soares JX, Rodrigues SSM, Santos JLM (2019) Tuning CdTe quantum dots reactivity for multipoint detection of Mercury(II), Silver(I) and Copper(II). J Lumin 207:386−396. https://doi.org/10.1016/j.jlumin.2018.11.035
Chen J, Wang N, Tong H, Song C, Ma H, Zhang Y, Gao F, Xu H, Wang W, Lou K (2021) A compact fluorescence/circular dichroism dual-modality probe for detection, differentiation, and detoxification of multiple heavy metal ions via bond-cleavage cascade reactions. Chin Chem Lett 32:3876−3881. https://doi.org/10.1016/j.cclet.2021.05.047
He Y, Wang Y, Mao G, Liang C, Fan M (2022) Ratiometric fluorescent nanoprobes based on carbon dots and multicolor CdTe quantum dots for multiplexed determination of heavy metal ions. Anal Chim Acta 1191:339251. https://doi.org/10.1016/j.aca.2021.339251
Wang S-e, Si S (2013) Aptamer biosensing platform based on carbon nanotube long-range energy transfer for sensitive, selective and multicolor fluorescent heavy metal ion analysis. Anal Methods 5:2947–2953. https://doi.org/10.1039/c3ay40360b
Deng Y, Chen Y, Zhou X (2018) Simultaneous sensitive detection of Lead(II), Mercury(II) and silver ions using a new nucleic acid-based fluorescence sensor. Acta Chim Slov 65:271−277. https://doi.org/10.17344/acsi.2017.3620
Lu Z, Wang P, Xiong W, Qi B, Shi R, Xiang D, Zhai K (2021) Simultaneous detection of Mercury (II), Lead (II) and Silver (I) based on fluorescently labelled aptamer probes and graphene oxide. Environ Technol 42:3065–3072. https://doi.org/10.1080/09593330.2020.1721565
Song J, Ma Q, Zhang S, Liu H, Guo Y, Feng F (2018) S,N-Co-doped carbon nanoparticles with high quantum yield for metal ion detection, IMP logic gates and bioimaging applications. New J Chem 42:20180‒20189. https://doi.org/10.1039/c8nj04527e
Pavadai R, Amalraj A, Subramanian S, Perumal P (2021) High catalytic activity of fluorophore-labeled Y-Shaped DNAzyme/3D MOF-MoS2NBs as a versatile biosensing platform for the simultaneous detection of Hg2+, Ni2+, and Ag+ ions. ACS Appl Mater Interfaces 13:31710–31724. https://doi.org/10.1021/acsami.1c07086
Wu Y-T, Zhao J-L, Mu L, Zeng X, Wei G, Redshaw C, Jin Z (2017) A 2-Styryl-1,8-Naphthyridine derivative as a versatile fluorescent probe for the selective recognition of Hg2+, Ag+ and F− ions by tuning the solvent. Sens Actuators B 252:1089–1097. https://doi.org/10.1016/j.snb.2017.06.057
Krishnaveni K, Iniya M, Siva A, Vidhyalakshmi N, Sasikumar S, Ramesh UKP, Murugesan S (2020) Naphthyl hydrazone anchored with nitrosalicyl moiety as fluorogenic and chromogenic receptor for heavy metals (Ag+, Hg2+) and biologically important F− Ion and its live cell imaging applications in HeLa cells zebrafish embryos. J Mol Struct 1217:128446. https://doi.org/10.1016/j.molstruc.2020.128446
Saleh N (2009) Luminescent sensor for Cd2+, Hg2+ and Ag+ in water based on a sulphur-containing receptor: Quantitative binding-softness relationship. Luminescence 24:30–34. https://doi.org/10.1002/bio.1058
Wang M, Meng G, Huang Q (2014) Iodeosin-based fluorescent and colorimetric sensing for Ag+, Hg2+, Fe3+ and further for halide ions in aqueous solution. RSC Adv 4:8055–8058. https://doi.org/10.1039/c3ra47928e
Mohanty P, Dash PP, Naik S, Behura R, Mishra M, Sahoo H, Sahoo SK, Barick AK, Jali BR (2023) A Thiourea-based fluorescent turn-on chemosensor for detecting Hg2+, Ag+ and Au3+ in aqueous medium. J Photochem Photobiol A 437:114491. https://doi.org/10.1016/j.photochem.2022.114491
He X, Jia K, Bai Y, Chen Z, Liu Y, Huang Y, Liu X (2021) Quantum dots encoded white-emitting polymeric superparticles for simultaneous detection of multiple heavy metal ions. J Hazard Mater 405:124263. https://doi.org/10.1016/j.jhazmat.2020.124263
Nie K, Dong B, Shi H, Liu Z, Liang B (2017) Thienyl Diketopyrrolopyrrole as a robust sensing platform for multiple ions and its application in molecular logic system. Sens Actuators B 244:849–853. https://doi.org/10.1016/j.snb.2017.01.037
Darroudi M, Ziarani GM, Ghasemi JB, Badiei A (2021) Facile and green preparation of colorimetric and fluorescent sensors for mercury, silver, and carbonate ions visual detecting: Spectroscopy and theoretical studies. J Mol Struct 1241:130626. https://doi.org/10.1016/j.molstruc.2021.130626
Sui N, Wang L, Yan T, Liu F, Sui J, Jiang Y, Wan J, Liu M, Yu WW (2014) Selective and sensitive biosensors based on metal-enhanced fluorescence. Sens Actuators B 202:1148–1153. https://doi.org/10.1016/j.snb.2014.05.122
Shi W, Sun S, Li X, Ma H (2010) Imaging different interactions of mercury and silver with live cells by a designed fluorescence probe rhodamine B selenolactone. Inorg Chem 49:1206–1210. https://doi.org/10.1021/ic902192a
Tsukamoto K, Shinohara Y, Iwasaki S, Maeda H (2011) A Coumarin-based fluorescent probe for Hg2+ and Ag+ with an N’-Acetylthioureido group as a fluorescence switch. Chem Commun 47:5073–5075. https://doi.org/10.1039/c1cc10933b
He X, Qing Z, Wang K, Zou Z, Shi H, Huang J (2012) Engineering a unimolecular multifunctional DNA probe for analysis of Hg2+ and Ag+. Anal Methods 4:345–347. https://doi.org/10.1039/c2ay05823e
Zhang X, Xu Y, Guo P, Qian X (2012) A dual channel chemodosimeter for Hg2+ and Ag+ Using a 1,3-Dithiane modified BODIPY. New J Chem 36:1621–1625. https://doi.org/10.1039/c2nj40242d
Fan J, Chen C, Lin Q, Fu N (2012) A fluorescent probe for the dual-channel detection of Hg2+/Ag+ and Its Hg2+-based complex for detection of mercapto biomolecules with a tunable measuring range. Sens Actuators B 173:874–881. https://doi.org/10.1016/j.snb.2012.08.004
Khatua S, Schmittel M (2013) A single molecular light-up sensor for quantification of Hg2+ and Ag+ in aqueous medium: high selectivity toward Hg2+ over Ag+ in a mixture. Org Lett 15:4422–4425. https://doi.org/10.1021/ol401970n
Lin G, Xu H, Cui Y, Wang Z, Yang Y, Qian G (2013) An ortho-methylated fluorescent chemosensor based on pyrromethene for highly selective and sensitive detection of Ag+ and Hg2+ ions. Mater Chem Phys 141:591–595. https://doi.org/10.1016/j.matchemphys.2013.06.0225
Wang Z-X, Ding S-N (2014) One-pot green synthesis of high quantum yield oxygen-doped, nitrogen-rich, photoluminescent polymer carbon nanoribbons as an effective fluorescent sensing platform for sensitive and selective detection of Silver(I) and Mercury(II) Ions. Anal Chem 86:7436−7445. https://doi.org/10.1021/ac501085d
Li F, Meng F, Wang Y, Zhu C, Cheng Y (2015) Polymer-based fluorescence sensor incorporating thiazole moiety for direct and visual detection of Hg2+ and Ag+. Tetrahedron 71:1700–1704. https://doi.org/10.1016/j.tet.2015.01.052
Hiruta Y, Koiso H, Ozawa H, Sato H, Hamada K, Yabushita S, Citterio D, Suzuki K (2015) Near IR emitting red-shifting ratiometric fluorophores based on borondipyrromethene. Org Lett 17:3022–3025. https://doi.org/10.1021/acs.orglett.5b01299
Wu Z, Feng M, Chen X, Tang X (2016) N-Dots as a photoluminescent probe for the rapid and selective detection of Hg2+ and Ag+ in aqueous solution. J Mater Chem B 4:2086–2089. https://doi.org/10.1039/c5tb02628h
Shi W, Chen Y, Chen X, Xie Z, Hui Y (2016) Simple-structured, hydrazinecarbothioamide derivatived dual-channel optical probe for Hg2+ and Ag+. J Lumin 174:56–62. https://doi.org/10.1016/j.jlumin.2016.01.032
Ren G, Zhang Q, Li S, Fu S, Chai F, Wang C, Qu F (2017) One pot synthesis of highly fluorescent N Doped C-Dots and used as fluorescent probe detection for Hg2+ and Ag+ in aqueous solution. Sens Actuators B 243:244−253. https://doi.org/10.1016/j.snb.2016.11.149
Maiti S, Prins LJ (2017) A modular self-assembled sensing system for heavy metal ions with tunable sensitivity and selectivity. Tetrahedron 73:4950–4954. https://doi.org/10.1016/j.tet.2017.05.028
Lee SY, Bok KH, Kim C (2017) A fluorescence, “turn-on” chemosensor for Hg2+ and Ag+ based on NBD (7-Nitrobenzo-2-Oxa-1,3-Diazolyl). RSC Adv 7:290–299. https://doi.org/10.1039/c6ra25585j
Zhou W, Ding J, Liu J (2017) 2-Aminopurine-Modified DNA homopolymers for robust and sensitive detection of mercury and silver. Biosens Bioelectron 87:171–177. https://doi.org/10.1016/j.bios.2016.08.033
Li Y, Liu Y, Zhou H, Chen W, Mei J, Su J (2017) Ratiometric Hg2+/Ag+ probes with orange red-white-blue fluorescence response constructed by integrating vibration-induced emission with an aggregation-induced emission motif. Chem Eur J 23:9280–9287. https://doi.org/10.1002/chem.201700945
Ravikumar A, Panneerselvam P, Morad N (2018) Metal-polydopamine framework as an effective fluorescent quencher for highly sensitive detection of Hg(II) and Ag(I) Ions through Exonuclease III activity. ACS Appl Mater Interfaces 10:20550–20558. https://doi.org/10.1021/acsami.8b05041
Zhu B, Ren G, Tang M, Chai F, Qu F, Wang C, Su Z (2018) Fluorescent silicon nanoparticles for sensing Hg2+ and Ag+ as well visualization of latent fingerprints. Dyes Pigm 149:686–695. https://doi.org/10.1016/j.dyepig.2017.11.041
Wei G, Jiang Y, Wang F (2018) A novel AIEE polymer sensor for detection of Hg2+ and Ag+ in aqueous solution. J Photochem Photobiol A 358:38–43. https://doi.org/10.1016/j.photochem.2018.03.006
Chen S, Wang W, Yan M, Tu Q, Chen S-W, Li T, Yuan M-S, Wang J (2018) 2-Hydroxy Benzothiazole modified rhodol: Aggreration-induced emission and dual-channel fluorescence sensing of Hg2+ and Ag+ Ions. Sens Actuators B 255:2086–2094. https://doi.org/10.1016/j.snb.2017.09.008
Zhang Y-M, Chen X-P, Liang G-Y, Zhong K-P, Lin Q, Yao H, Wei T-B (2018) A novel water soluble pillar[5]arene and phenazine derivative self-assembled pseudorotaxane sensor for the selective detection of Hg2+ and Ag+ with high selectivity and sensitivity. New J Chem 42:10148–10152. https://doi.org/10.1039/c8nj00508g
Luo L, Wang P, Wang Y, Wang F (2018) pH assisted selectice detection of Hg(II) and Ag(I) based on nitrogen-rich carbon dots. Sens Actuators B 273:1640–1647. https://doi.org/10.1016/j.snb.2018.07.090
Ye F, Liang X-M, Xu K-X, Pang X-X, Chai Q, Fu Y (2019) A novel dithiourea-appended naphthalimide “on-off” fluorescent probe for detecting Hg2+ and Ag+ and its application in cell imaging. Talanta 200:494–502. https://doi.org/10.1016/j.talanta.2019.03.076
Chen Y-J, Chen M-Y, Lee K-T, Shen L-C, Hung H-C, Niu H-C, Chung W-S (2020) 1,3-Alternate Calix[4]arene functionalized with pyrazole and triazole ligands as a highly selective fluorescent sensor for Hg2+ and Ag+ ions. Front Chem 8:593261. https://doi.org/10.3389/fchem.2020.593261
Huang N-H, Liu Y, Li R-T, Chen J, Hu P-P, Young DJ, Chen J-X, Zhang W-H (2020) Sequential Ag+/Biothiol and synchronous Ag+/Hg2+ biosensing with Zwitterionic Cu2+-based metal-organic frameworks. Analyst 145:2779–2788. https://doi.org/10.1039/d0an00002g
Khoshbin Z, Housaindokht MR, Verdian A (2020) A low-cost paper-based aptasensor for simultaneous trace-level monitoring of Mercury (II) and Silver (I) ions. Anal Biochem 597:113689. https://doi.org/10.1016/j.ab.2020.113689
Saiyasombat W, Kiatisevi S (2021) Bis-BODIPY linked-triazole based on catechol core for selective dual detection of Ag+ and Hg2+. RSC Adv 11:3703–3712. https://doi.org/10.1039/d0ra09686e
Correia C, Martinho J, Maçôas E (2022) A fluorescent nanosensor for Silver (Ag+) and Mercury (Hg2+) ions using Eu(III)-Doped carbon dots. Nanomaterials 12:385. https://doi.org/10.3390/nano12030385
Cao Q-W, Yue T-C, Dong Q-W, Ma Q-C, Xie Z-B, Wang D-Z, Wang L-L (2023) Effective detection of Ag+, Hg2+ and dye adsorption properties of Ln-MOFs based on a benzimidazole carboxylic acid ligand. Dalton Trans 52:6008–6018. https://doi.org/10.1039/d3dt00579h
Zheng T, Xu Z, Zhao Y, Li H, Jian R, Lu C (2018) Multiresponsive polysiloxane bearing photochromic spirobenzopyran for sensing pH changes and Fe3+ Ions and sequential sensing of Ag+ and Hg2+ ions. Sens Actuators B 255:3305–3315. https://doi.org/10.1016/j.snb.2017.09.158
Qi Y, Li Y, Nan T, Li H, Tang J, Liu S, Wang Y (2022) A novel fluorescent probe with large stokes shift for the detection of Ag+ and Hg2+. Opt Mater 123:111929. https://doi.org/10.1016/j.optmat.2021.111929
Jiang L, Zheng T, Xu Z, Li J, Li H, Tang J, Liu S, Wang Y (2022) New NIR spectroscopic probe with a large stokes shift for Hg2+ and Ag+ detection and living cells imaging. Spectrochim Acta A 271:120916. https://doi.org/10.1016/j.saa.2022.120916
Hu C-F, Zhang P-L, Sui Y-F, Lv J-S, Ansari MF, Battini N, Li S, Zhou C-H, Geng R-X (2020) Ethylenic conjugated coumarin thiazolidinediones as new efficient antimicrobial modulators against clinical methicillin-resistant Staphylococcus aureus. Bioorg Chem 94:103434. https://doi.org/10.1016/j.bioorg.2019.103434
Munive L, Gómez-Calvario V, Olivo HF (2017) Manganese triacetate oxidation of methyl 1-Hydroxy-2-Naphthalene carboxylates. Tetrahedron Lett 58:2445–2447. https://doi.org/10.1016/j.tetlet.2017.05.028
Hao C, Xua L, Xing C, Kuang H, Wang L, Xu C (2012) Oligonucleotide-based fluorogenic sensor for simultaneous detection of heavy metal ions. Biosens Bioelectron 36:174–178. https://doi.org/10.1016/j.bios.2012.04.008
Nandre JP, Patil SR, Sahoo SK, Pradeep CP, Churakov A, Yu F, Chen L, Redshaw C, Patil AA, Patil UD (2017) A chemosensor for micro- and nano-molar detection of Ag+ and Hg2+ ions in pure aqueous media and its applications in cell imaging. Dalton Trans 46:14201–14209. https://doi.org/10.1039/c7dt02524f
Chen Z-E, Zhang H, Iqbal Z (2019) A new thiosemicarbazone fluorescent probe based on 9,9’-Bianthracene for Hg2+ and Ag+. Spectrochim Acta A 215:34–40. https://doi.org/10.1016/j.saa.2019.02.036
Xiao L, Liu K, Duan L, Cheng X (2021) Reaction-based fluorescent silk probes with high sensitivity and selectivity to Hg2+ and Ag+ ions. J Mater Chem C 9:4877–4887. https://doi.org/10.1039/d0tc05429a
Jagadhane KS, Bhosale SR, Gunjal DB, Nille OS, Kolekar GB, Kolekar SS, Dongale TD, Anbhule PV (2022) Tetraphenylethene-based fluorescent chemosensor with mechanochromic and aggregation-induced emission (AIE) properties for the selective and sensitive detection of Hg2+ and Ag+ ions in aqueous media: Application to environmental analysis. ACS Omega 7:34888–34900. https://doi.org/10.1021/acsomega.2c03437
Mahata S, Kumar S, Dey S, Mandal BB, Manivannan V (2022) A Probe with Hydrazinecarbothioamide and 1,8-Naphthalimide groups for “turn-on” fluorescence detection of Hg2+ and Ag+ ions and live-cell imaging studies. Inorg Chim Acta 535:120876. https://doi.org/10.1016/j.ica.2022.120876
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The Funding for the Open Research Program of State Key Laboratory of Molecular Engineering of Polymers, Fudan University (K2022-38 to Yanxi Song) is acknowledged.
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Hongqi Li, Jiabao Yan and Lin Jiang wrote the main manuscript text; Jiabao Yan, Lin Jiang and Yong Zhao performed research and analyzed the data. Yanxi Song, Jirui Yu and Lang Cheng prepared the figures. All authors reviewed the manuscript.
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Li, H., Yan, J., Jiang, L. et al. Selective and Sensitive Detection of Hg2+ and Ag+ by a Fluorescent and Colorimetric Probe with Large Stokes Shift. J Fluoresc (2023). https://doi.org/10.1007/s10895-023-03478-8
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DOI: https://doi.org/10.1007/s10895-023-03478-8