Abstract
A new phenanthroimidazole-based fluorescence probe for selective detection of HClO was synthesized and characterized using 1HNMR, 13CNMR, IR, and HRMS. With benzenesulfonohydrazide as the identification group, the probe demonstrated a fast fluorescence response from yellow-green to blue when the HC = N double bond was oxidized and broken into an aldehyde group by HClO. The probe showed high selectivity and sensitivity towards HClO with approximately 4.5-fold fluorescence enhancement and has been successfully applied in the molecular logic gate, determination of HClO in environmental water samples, and portable HClO detection.
Graphical Abstract
Similar content being viewed by others
Availability of Data and Materials
Data will be made available on request.
References
Okunaka S, Miseki Y, Sayama K (2022) Controlling the selectivity of solar O2/HClO production from seawater by simple surface modification of visible-light responsible photoelectrodes. J Ceram Soc Jpn 130:395–402. https://doi.org/10.2109/jcersj2.21175
Ferro EI, Ruuttunen K, Perrin J, Vuorinen T (2021) Sustainable bleaching of Eucalyptus sp. kraft pulp with hypochlorous acid, ozone and hydrogen peroxide. Ind Crops Prod 172:114004. https://doi.org/10.1016/j.indcrop.2021.114004
Len SV, Hung YC, Erickson M, Kim C (2000) Ultraviolet spectrophotometric characterization and bactericidal properties of electrolyzed oxidizing water as influenced by amperage and pH. J Food Prot 63:1534–1537. https://doi.org/10.4315/0362-028x-63.11.1534
Remucal CK, Manley D (2016) Emerging investigators series: the efficacy of chlorine photolysis as an advanced oxidation process for drinking water treatment. Environ Sci Water Res Technol 2:565–579. https://doi.org/10.1039/c6ew00029k
Vianna ME, Gomes BP, Berber VB, Zaia AA, Ferraz CC, de Souza-Filho FJ (2004) In vitro evaluation of the antimicrobial activity of chlorhexidine and sodium hypochlorite. Oral Surg Oral Med Oral Pathol Oral Radiol Endod 97:79–84. https://doi.org/10.1016/s1079-2104(03)00360-3
Song H, Zhou Y, Xu C, Wang X, Zhang J, Wang Y, Liu X, Guo M, Peng X (2019) A dual-function fluorescent probe: sensitive detection of water content in commercial products and rapid detection of hypochlorite with a large Stokes shift. Dyes Pigm 162:160–167. https://doi.org/10.1016/j.dyepig.2018.10.023
Fang FC (2004) Antimicrobial reactive oxygen and nitrogen species: concepts and controversies. Nat Rev Microbiol 2:820–832. https://doi.org/10.1038/nrmicro1004
Taheri M, Mansour N (2019) Functionalized silicon nanoparticles as fluorescent probe for detection of hypochlorite in water. J Photochem Photobiol A 382:111906. https://doi.org/10.1016/j.jphotochem.2019.111906
Wang W, ** L, Shen Z, Li Z, Zhang X, Wang Q (2019) A fluorescent probe with a significant selective turn-on response for HClO detection and bioimaging in living cells. ChemistrySelect 4:7425–7430. https://doi.org/10.1002/slct.201901587
Wang N, Yu K, Shan Y, Li K, Tian J, Yu X, Wei X (2020) HClO/ClO–indicative interpenetrating polymer network hydrogels as intelligent bioactive materials for wound healing. ACS Appl Bio Mater 3:37–44. https://doi.org/10.1021/acsabm.9b00806
Winterbourn CC, Hampton MB, Livesey JH, Kettle AJ (2006) Modeling the reactions of superoxide and myeloperoxidase in the neutrophil phagosome: implications for microbial killing. J Biol Chem 281:39860–39869. https://doi.org/10.1074/jbc.M605898200
Hampton MB, Kettle AJ, Winterbourn CC (1998) Inside the neutrophil phagosome: oxidants, myeloperoxidase, and bacterial killing. Blood 92:3007–3017. https://doi.org/10.1182/blood.v92.9.3007.421k47-3007-3017
Bag S, Tseng JC, Rochford J (2015) A BODIPY-luminol chemiluminescent resonance energy-transfer (CRET) cassette for imaging of cellular superoxide. Org Biomol Chem 13:1763–1767. https://doi.org/10.1039/c4ob02413c
Song X, Shen H, Yin X, Wang X, Liu J (2013) Microflow-injection chemiluminescence of luminol and hypochlorite enhanced by phloxine B. Luminescence 28:16–22. https://doi.org/10.1002/bio.1388
Lin Q, Huang Y, Fan X, Zheng X, Chen X, Zhan X, Zheng H (2017) A ratiometric fluorescent probe for hypochlorous acid determination: excitation and the dual-emission wavelengths at NIR region. Talanta 170:496–501. https://doi.org/10.1016/j.talanta.2017.04.024
Ren M, Nie J, Deng B, Zhou K, Wang JY, Lin W (2017) A fluorescent probe for ratiometric imaging of exogenous and intracellular formed hypochlorous acid in lysosomes. New J Chem 41:5259–5262. https://doi.org/10.1039/c7nj00949f
Soldatkin AP, Gorchkov DV, Martelet C, Jaffrezic-Renault N (1997) New enzyme potentiometric sensor for hypochlorite species detection. Sens Actuators B 43:99–104. https://doi.org/10.1016/s0925-4005(97)00144-5
Jackson DS, Crockett DF, Wolnik KA (2006) The indirect detection of bleach (sodium hypochlorite) in beverages as evidence of product tampering. J Forensic Sci 51:827–831. https://doi.org/10.1111/j.1556-4029.2006.00160.x
Zhang R, Song B, Yuan J (2018) Bioanalytical methods for hypochlorous acid detection: recent advances and challenges. TrAC Trends Anal Chem 99:1–33. https://doi.org/10.1016/j.trac.2017.11.015
He X, Wu C, Qian Y, Li Y, Ding F, Zhou Z, Shen J (2019) Symmetrical bis-salophen probe serves as a selectively and sensitively fluorescent switch of gallium ions in living cells and zebrafish. Talanta 205:120118. https://doi.org/10.1016/j.talanta.2019.120118
Feng S, Liu D, Feng W, Feng G (2017) Allyl fluorescein ethers as promising fluorescent probes for carbon monoxide imaging in living cells. Anal Chem 89:3754–3760. https://doi.org/10.1021/acs.analchem.7b00135
Zhang P, Wang H, Zhang D, Zeng X, Zeng R, **ao L, Tao H, Long Y, Yi P, Chen J (2018) Two-photon fluorescent probe for lysosome-targetable hypochlorous acid detection within living cells. Sens Actuators B 255:2223–2231. https://doi.org/10.1016/j.snb.2017.09.025
Liu D, Du M, Chen D, Ye K, Zhang Z, Liu Y, Wang Y (2015) A novel tetraphenylsilane-phenanthroimidazole hybrid host material for highly efficient blue fluorescent, green and red phosphorescent OLEDs. J Mater Chem C 3:4394–4401. https://doi.org/10.1039/c5tc00333d
Zhao Y, Li H, Xue Y, Ren Y, Han T (2017) A phenanthroimidazole-based fluorescent probe for hypochlorous acid with high selectivity and its bio-imaging in living cells. Sens Actuators B 241:335–341. https://doi.org/10.1016/j.snb.2016.10.092
Yang X, Zheng Y, Zheng L (2022) A phenanthroimidazole-based fluorescent probe for ratiometric detection of ClO-. J Photochem Photobiol A 424:113575. https://doi.org/10.1016/j.jphotochem.2021.113575
Lin W, Long L, Chen B, Tan W (2009) A ratiometric fluorescent probe for hypochlorite based on a deoximation reaction. Chemistry 15:2305–2309. https://doi.org/10.1002/chem.200802054
Guo J, Zhang Z, Kuai Z, Wang R, Yang Q, Shan Y, Li Y (2017) A new turn-on fluorescent probe towards hypochlorite in living cells. Anal Methods 9:864–870. https://doi.org/10.1039/c6ay02819e
Dou K, Fu Q, Chen G, Yu F, Liu Y, Cao Z, Li G, Zhao X, **a L, Chen L, Wang H, You J (2017) A novel dual-ratiometric-response fluorescent probe for SO2/ClO- detection in cells and in vivo and its application in exploring the dichotomous role of SO2 under the ClO- induced oxidative stress. Biomaterials 133:82–93. https://doi.org/10.1016/j.biomaterials.2017.04.024
Shen Y, Yang Y, Gu B (2020) A novel fluorescent probe based on phenanthroimidazole for hypochlorite and its cell imaging application. J Instrumental Anal 39:961–966. https://doi.org/10.3969/j.issn.1004-4957.2020.08.003
Katz E, Privman V (2010) Enzyme-based logic systems for information processing. Chem Soc Rev 39:1835–1857. https://doi.org/10.1039/B806038J
Kolanowski JL, Liu F, New EJ (2018) Fluorescent probes for the simultaneous detection of multiple analytes in biology. Chem Soc Rev 47:195–208. https://doi.org/10.1039/C7CS00528H
Kong F, Liu Q, Wu X, Wang Z, Chen Q, Chen L (2011) 2-(4-Formylphenyl)phenanthroimidazole as a colorimetric and fluorometric probe for selective fluoride ion sensing. J Fluoresc 21:1331–1335. https://doi.org/10.1007/s10895-011-0858-7
Li X, Zhang G, Ma H, Zhang D, Li J, Zhu D (2004) 4,5-Dimethylthio-4 ’-[2-(9-anthryloxy)ethylthio]tetrathiafulvalene, a highly selective and sensitive chemiluminescence probe for singlet oxygen. J Am Chem Soc 126:11543–11548. https://doi.org/10.1021/ja0481530
Maity S, Das S, Sadlowski CM, Zhang J, Vegesna GK, Murthy N (2017) Thiophene bridged hydrocyanine-a new fluorogenic ROS probe. Chem Commun 53:10184–10187. https://doi.org/10.1039/c7cc04847e
Chen G, Song F, Wang J, Yang Z, Sun S, Fan J, Qiang X, Wang X, Dou B, Peng X (2012) FRET spectral unmixing: a ratiometric fluorescent nanoprobe for hypochlorite. Chem Commun 48:2949–2951. https://doi.org/10.1039/c2cc17617c
Chen X, Wang F, Hyun JY, Wei T, Qiang J, Ren X, Shin I, Yoon J (2016) Recent progress in the development of fluorescent, luminescent and colorimetric probes for detection of reactive oxygen and nitrogen species. Chem Soc Rev 45:2976–3016. https://doi.org/10.1039/c6cs00192k
Yang X, Shi W, Dong X, Cui C, Huang X, Wang X, **e H, Li Y, Yan M, Cui Y, Sun G (2020) A simple but sensitive and efficient fluorescent probe for “turn-on” sensing of ClO-. Polyhedron 185:114563. https://doi.org/10.1016/j.poly.2020.114563
Cheng G, Fan J, Sun W, Sui K, ** X, Wang J, Peng X (2013) A highly specific BODIPY-based probe localized in mitochondria for HClO imaging. Analyst 138:6091–6096. https://doi.org/10.1039/c3an01152f
Al-Awadi H, Ibrahim MR, Al-Awadi NA, Ibrahim YA (2007) Gas-phase thermolysis of condensed-1,2,4-triazines: interesting routes toward heterocyclic ring systems. Tetrahedron 63:12948–12953. https://doi.org/10.1016/j.tet.2007.10.040
You J, Zhao X, Suo Y, Li Y, Wang H, Chen G (2007) Determination of long-chain fatty acids in bryophyte plants extracts by HPLC with fluorescence detection and identification with MS. J Chromatogr B Analyt Technol Biomed Life Sci 848:283–291. https://doi.org/10.1016/j.jchromb.2006.10.025
Ding H, Pu Y, Ye D, Dong Z, Yang M, Lu C, An Y (2020) The design and synthesis of two imidazole fluorescent probes for the special recognition of HClO/NaHSO3 and their applications. Anal Methods 12:2476–2483. https://doi.org/10.1039/d0ay00334d
Author information
Authors and Affiliations
Contributions
All authors contributed to the study's conception and design. Material preparation, data collection, and analysis were performed by Enhui Dai and Yumiao Sheng. The first draft of the manuscript was written by Enhui Dai. The conceptualization, resources, supervision, and writing-review & editing were performed by Yunling Gao. All authors read and approved the final manuscript.
Corresponding author
Ethics declarations
Ethical Approval
Not applicable.
Competing Interests
The authors have no financial interests or potential conflicts of interest to disclose.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Highlights
• Probe PIBH showed good selectivity for HClO over other reactive oxygen species and reactive nitrogen species.
• It was easy to synthesize and demonstrated the fast fluorescence increase by HClO.
• The intensity at 436 nm had linear relationship with concentrations of HClO in the range of 0-1000 μM with the detection limit of 6.74 μM.
• A molecular logic gate combining AND and OR was established.
Supplementary Information
Below is the link to the electronic supplementary material.
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
Dai, E., Sheng, Y. & Gao, Y. A Fast-Response, Phenanthroimidazole-Based Fluorescent Probe for Selective Detection of HClO. J Fluoresc (2023). https://doi.org/10.1007/s10895-023-03376-z
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s10895-023-03376-z