Abstract
Merocyanine 540 dye (MC 540) has been demonstrated as a ‘turn-off’ fluorescent probe to detect hypochlorite ions (ClO−) in an aqueous medium. MC 540 was separately investigated by fluorescence and absorption spectroscopy in the presence of various analytes, including cations and anions. It was revealed that the fluorescence intensity of MC 540 was effectively quenched with only ClO− ions without being affected by the other twenty-five analytes. This was also observed with the naked eye, and the color of MC 540 changed from pink to colorless in the presence of only ClO− ions. Moreover, fluorescence interference experiments were performed for ClO−. MC 540 was found to detect ClO− independently of other analytes. The interaction ratio between MC 540 and ClO− was determined as 4:1, and the binding constant (Ka) was calculated as 28.38 M−4 for MC 540. The detection limit (LOD) of ClO− was determined to be 6.83 nM. The presented method was reliably applied to drinking, natural spring, and tap water samples. Thus, it has been proven that the MC 540 can be used as a sensitive, selective, color-changeable, and easy-to-apply ‘turn-off’ fluorescence sensor to detect ClO− in a specific concentration range.
Graphical abstract
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Ahmmed E, Lohar S, Ghatak S, Hira SK, Manna PP, Chattopadhyay P (2019) Development of a selective reaction-based turn-on fluorosensor and biomarker for hypochlorite ions in aqueous media. Anal Methods 11:2415–2421. https://doi.org/10.1039/c9ay00325h
Alanazi RS, Laref A (2022) Monte Carlo simulations of photodynamic therapy in human blood model. Lasers Med Sci 37:1515–1529. https://doi.org/10.1007/s10103-021-03383-1
Bialas D, Zhong CW, Wurthner F, Spano FC (2019) Essential states model for merocyanine dye stacks: bridging electronic and optical absorption properties. J Phys Chem C 123:18654–18664. https://doi.org/10.1021/acs.jpcc.9b04430
Brouwer AM (2011) Standards for photoluminescence quantum yield measurements in solution (IUPAC Technical Report). Pure Appl Chem 83:2213–2228. https://doi.org/10.1351/Pac-Rep-10-09-31
Bu Y, Yu L, Su P, Wang L, Sun Z, Sun M, Wang X, Huang D, Wang S (2022) Green-emitting carbon quantum dots as a dual-mode fluorescent and colorimetric sensor for hypochlorite. Anal Bioanal Chem 414:2651–2660. https://doi.org/10.1007/s00216-022-03901-2
Clayden J, Greeves N, Warren S (2012) Organic chemistry, 2nd edn. England, Oxford University Press, London
Ding YJ, Ling J, Cai JF, Wang SP, Li XM, Yang MH, Zha L, Yan J (2016) A carbon dot-based hybrid fluorescent sensor for detecting free chlorine in water medium. Anal Methods 8:1157–1161. https://doi.org/10.1039/c5ay03143e
Domask WG, Kobe KA (1954) Synthesis of ethylene chlorohydrin. Ind Eng Chem 46:680–689. https://doi.org/10.1021/ie50532a028
Guo X, Li S, Mu S, Zhang Y, Liu X, Zhang H (2020) A merocyanine-based dual-mode optical probe for detection of hydrazine and its bioimaging application in vitro and vivo. Spectrochim Acta A Mol Biomol Spectrosc 226:117625. https://doi.org/10.1016/j.saa.2019.117625
Jacobsen EN, Zhang W, Muci AR, Ecker JR, Deng L (1991) Highly enantioselective epoxidation catalysts derived from 1, 2-diaminocyclohexane. JACS 113:7063–7064. https://doi.org/10.1021/ja00018a068
Jia XJ, Wang TB, Bu XD, Tu Q, Spencer S, Gong XY, Natishan T (2005) Study of hypochlorite-specific enhancement in ICP-AES and ICP-MS. J Anal Atom Spectrom 20:1293–1295. https://doi.org/10.1039/b504846j
Jiang QW, Jing Y, Ni YY, Gao RS, Zhou PY (2020) Potentiality of carbon quantum dots derived from chitin as a fluorescent sensor for detection of ClO−. Microchem J 157:105111. https://doi.org/10.1016/j.microc.2020.105111
Khurana R, Barooah N, Bhasikuttan AC, Mohanty J (2019) Supramolecular assembly induced emission of thiazole orange with sulfobutylether beta-cyclodextrin: a stimuli-responsive fluorescence sensor for tyramine. Chem Phys Chem 20:2498–2505. https://doi.org/10.1002/cphc.201900656
Kim HJ, Jung IS, Jung S, Kim D, Minami D, Byun S, Choi T, Shin J, Yun S, Heo CJ, Park KB, Park SY, Lim SJ, Lee HS, Choi B (2022) Harnessing intramolecular chalcogen-chalcogen bonding in merocyanines for utilization in high-efficiency photon-to-current conversion optoelectronics. ACS Appl Mater Interfaces 14:4360–4370. https://doi.org/10.1021/acsami.1c16950
Korkmaz K, Beser BM, Senol AM, Onganer Y (2021) Safranin T- SDS- GO ternary system: a fluorescent pH sensor. Colloids Surf B 206:111977. https://doi.org/10.1016/j.colsurfb.2021.111977
Kronenberg NM, Deppisch M, Wurthner F, Lademann HW, Deing K, Meerholz K (2008) Bulk heterojunction organic solar cells based on merocyanine colorants. Chem Commun. https://doi.org/10.1039/b813341g
Li Y, He Y, Ge Y, Song G, Zhou J (2021a) Smartphone-assisted visual ratio-fluorescence detection of hypochlorite based on copper nanoclusters. Spectrochim Acta A Mol Biomol Spectrosc 255:119740. https://doi.org/10.1016/j.saa.2021.119740
Li YB, Wu F, Han MM, Li Z, Zhu LN, Li ZA (2021b) Merocyanine with hole-transporting ability and efficient defect passivation effect for perovskite solar cells. ACS Energy Lett 6:869–876. https://doi.org/10.1021/acsenergylett.1c00124
Liu Y, Zheng X, Zhou J, Xie Z (2021) Merocyanine-paclitaxel conjugates for photothermal induced chemotherapy. J Mater Chem B 9:2334–2340. https://doi.org/10.1039/d0tb02569k
Liu L, Yang YX, Cui YY, Zhu WJ, Fang M, Li C (2023) A novel dicyanisophorone-based colorimetric and ratiometric fluorescent probe for the detection of hypochlorite in the environment and living cells. Dyes Pigm 208:110879. https://doi.org/10.1016/j.dyepig.2022.110879
Lohar S, Patra A, Roy P, Babu SPS, Chattopadhyay P (2018) A highly selective fluorescence turn-on probe for the sensing and bioimaging of hypochlorite anion in aqueous media. Chem Select 3:6707–6713. https://doi.org/10.1002/slct.201800114
Pervaiz S (2001) Reactive oxygen-dependent production of novel photochemotherapeutic agents. FASEB J 15:612–617. https://doi.org/10.1096/fj.00-0555rev
Ponnuvel K, Ramamoorthy J, Sivaraman G, Padmini V (2018) Merocyanine dye-based fluorescent chemosensor for highly selective and sensitive detection of hypochlorous acid and imaging in live cells. Chem Select 3:91–95. https://doi.org/10.1002/slct.201701833
Ray A, Mohan JM, Amreen K, Dubey SK, Javed A, Ponnalagu RN, Goel S (2022) Ink-jet-printed CuO nanoparticle-enhanced miniaturized paper-based electrochemical platform for hypochlorite sensing. Appl Nanosci 13:1855–1861. https://doi.org/10.1007/s13204-021-02235-2
Santacesaria E, Vitiello R, Tesser R, Russo V, Turco R, Di Serio M (2014) Chemical and technical aspects of the synthesis of chlorohydrins from glycerol. Ind Eng Chem Res 53:8939–8962. https://doi.org/10.1021/ie403268b
Şenol AM, Bozkurt E (2023) A green “off–on” fluorescent sensor to detect Fe3+ and ATP using synthesized carbon dots from rosehip. Res Chem Intermed 49:2175–2189. https://doi.org/10.1007/s11164-023-04960-5
Şenol AM, Onganer Y (2022) A novel “turn-off” fluorescent sensor based on cranberry derived carbon dots to detect iron (III) and hypochlorite ions. J Photochem Photobiol A 424:113655. https://doi.org/10.1016/j.jphotochem.2021.113655
Şenol AM, Onganer Y, Meral K (2017) An unusual “off-on” fluorescence sensor for iron(III) detection based on fluorescein–reduced graphene oxide functionalized with polyethyleneimine. Sens Actuators, B Chem 239:343–351. https://doi.org/10.1016/j.snb.2016.08.025
Şenol AM, Kassa SB, Onganer Y (2023) A simple fluorescent “Turn off-on” sensor based on P, N-doped graphene quantum dots for Hg2+ and cysteine determination. Sens Actuator A Phys 356:114362. https://doi.org/10.1016/j.sna.2023.114362
Simões EFC, Leitão JMM, da Silva JCGE (2016) Carbon dots prepared from citric acid and urea as fluorescent probes for hypochlorite and peroxynitrite. Mikrochim Acta 183:1769–1777. https://doi.org/10.1007/s00604-016-1807-6
Sinikova NA, Shaydullina GM, Lebedev AT (2014) Comparison of chlorine and sodium hypochlorite activity in the chlorination of structural fragments of humic substances in water using GC-MS. J Anal Chem 69:1300–1306. https://doi.org/10.1134/S106193481414010x
Vijay K, Nandi C, Samant SD (2014) Synthesis of a dihydroquinoline based merocyanine as a ‘naked eye’ and ‘fluorogenic’ sensor for hydrazine hydrate in aqueous medium and hydrazine gas. RSC Adv 4:30712–30717. https://doi.org/10.1039/c4ra02426e
Wang PL, Tao BY (1998) Soy fatty acid oxidation with sodium hypochlorite monitored by nuclear magnetic resonance spectroscopy. JAOCS 75:9–14. https://doi.org/10.1007/s11746-998-0002-2
Wang Y, Zhang P, Lu Q, Wang Y, Fu W, Tan Q, Luo W (2018) Water-soluble MoS2 quantum dots are a viable fluorescent probe for hypochlorite. Mikrochim Acta 185:233. https://doi.org/10.1007/s00604-018-2768-8
Watanabe T, Idehara T, Yoshimura Y, Nakazawa H (1998) Simultaneous determination of chlorine dioxide and hypochlorite in water by high-performance liquid chromatography. J Chromatogr A 796:397–400. https://doi.org/10.1016/S0021-9673(97)01009-1
Winterbourn CC, van den Berg JJ, Roitman E, Kuypers FA (1992) Chlorohydrin formation from unsaturated fatty acids reacted with hypochlorous acid. Arch Biochem Biophys 296:547–555. https://doi.org/10.1016/0003-9861(92)90609-z
Wu G, Zeng F, Wu S (2013) A water-soluble and specific BODIPY-based fluorescent probe for hypochlorite detection and cell imaging. Anal Methods 5:5589–5596. https://doi.org/10.1039/C3AY41268G
Xiao K, Nie HM, Gong CB, Ou XX, Tang Q, Chow CF (2015) A colorimetric and fluorescent dual-channel cyanide ion probe using crosslinked polymer microspheres functionalized with protonated Brooker’s merocyanine. Dyes Pigm 116:82–88. https://doi.org/10.1016/j.dyepig.2015.01.015
Xie L, Zheng R, Hu H, Li L (2022) Determination of hypochlorite and bisulfite in water by bifunctional colorimetric sensor based on octupolar conjugated merocyanine dyes. Microchem J 172:106931. https://doi.org/10.1016/j.microc.2021.106931
Yuan Y, Yan J, Liu J, Wang Y, Chen Y (2023) Ex_g-C3N4 as a novel fluorescent probe for sensitive detecting ClO− in water samples with portable test strip. Anal Chim Acta 1239:340715. https://doi.org/10.1016/j.aca.2022.340715
Zhou Y, Xu HJ, Li XJ, Lu CW, An Y (2022) Synthesis and mechanism study of two similar colorimetric fluorescent probes for specific detection of bisulfite and hypochlorite. Res Chem Intermed 48:85–100. https://doi.org/10.1007/s11164-021-04625-1
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest
The corresponding author states that there is no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Supplementary file2 (MP4 77428 KB)
Rights and permissions
Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.
About this article
Cite this article
Şenol, A.M. An easy-to-apply fluorescent sensor for ClO− determination using merocyanine 540 in aqueous medium. Chem. Pap. 78, 2043–2052 (2024). https://doi.org/10.1007/s11696-023-03231-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-023-03231-2