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A Novel Diarylethene-rhodamine Unit Based Chemosensor for Fluorimetric and Colorimetric Detection of Hg2+

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Abstract

A novel fluorimetric and colorimetric chemosensor (1O) was synthesized with diarylethene-rhodamine unit and characterized by ESI–MS, 1H NMR, and 13C NMR. The chemosensor can selectively recognize extremely low concentrations of Hg2+ over a variety of metal ions with remarkable colorimetric and fluorescent responses. The colorimetric and fluorescent changes were ascribed the reaction between 1O and Hg2+ destructed the rhodamine hydrazide into open-ring form which was proved by mass spectrometry and nuclear magnetic titration analyses. The detection limits of the UV absorption and fluorescence methods for Hg2+ were found to be 0.708 μM and 24.6 nM, respectively. Moreover, the chemosensor exhibited excellent photochromism and outstanding fatigue resistance property under alternating UV and visible light irradiation. The application potential of the chemosensor was demonstrated with the qualitative detection of Hg2+ in real water samples.

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Data Availability

The datasets generated during and/or analysed during the current study are available from the corresponding author on reasonable request.

References

  1. Ren MG, Deng BB, Wang JY, Liu ZR, Lin WY (2015) A dual-emission fluorescence-enhanced probe for imaging copper (II) ions in lysosomes. J Mater Chem B 3:6746–6752. https://doi.org/10.1039/c5tb01184a

    Article  CAS  PubMed  Google Scholar 

  2. Wang CC, Liu YQ, Cheng JY, Song JH, Zhao YF, Ye Y (2015) Efficient FRET-based fuorescent ratiometric chemosensors for Fe3+ and its application in living cells. Journal of Luminescence 157:143–148. https://doi.org/10.1016/j.jlumin.2014.08.039

    Article  CAS  Google Scholar 

  3. Patnaik R, Padhy RN (2018) Comparative study on toxicity of methylmercury chloride and methylmercury hydroxide to the human neuroblastoma cell line SH-SY5Y. Environmental Science and Pollution Research International 25:20606–20614. https://doi.org/10.1007/s11356-018-2164-2

    Article  CAS  PubMed  Google Scholar 

  4. de Freitas AS, Funck VR, Rotta Mdos S, Bohrer D, Morschbacher V, Puntel RL, Nogueira CW, Farina M, Aschner M, Rocha JBT (2009) Diphenyl diselenide a simple organoselenium compound, decrease methylmercury-induced cerebral, hepatic and renal oxidative stress and mercury deposition in adult mice. Brain Research Bulletin 79:77–84. https://doi.org/10.1016/j.brainresbull.2008.11.001

    Article  CAS  PubMed  Google Scholar 

  5. Dan W, Deng XK, Yu YH (2019) A novel turn-on fluorescent probe for Hg2+ detection based on rhodamine B spirolactam derivative. International Journal of Environmental Analytical Chemistry 99:1515–1527. https://doi.org/10.1080/03067319.2019.1625339

    Article  CAS  Google Scholar 

  6. Mahato P, Saha S, Suresh E, Di Liddo R, Parnigotto PP, Conconi MT, Kesharwani MK, Ganguly B, Das A (2012) Ratiometric detection of Cr3+ and Hg2+ by a Naphthalimide-rhodamine based fluorescent probe. Inorganic Chemistry 51:1769–1777. https://doi.org/10.1021/ic202073q

    Article  CAS  PubMed  Google Scholar 

  7. Kraithong S, Sirirak J, Soisuwan K, Wanichacheva N, Swanglap P (2018) Enhancing sensitivity of novel Hg2+ fluorescent sensor via plasmonic enhancement of silver nanoparticles. Sensors and Actuators B: Chemical 258:694–703. https://doi.org/10.1016/j.snb.2017.11.049

    Article  CAS  Google Scholar 

  8. Tang X, Wang Y, Han J, Ni L, Zhang HQ, Li C, Li J, Qiu Y (2018) A novel fluorescent probe based on biphenyl and rhodamine for multi-metal ion recognition and its application. Dalton Transactions 47:3378–3387. https://doi.org/10.1039/c7dt04629d

    Article  CAS  PubMed  Google Scholar 

  9. Rani BK, John SA (2018) Fluorogenic mercury ion sensor based on pyrene-amino mercapto thiadiazole unit. Journal of Hazardous Materials 343:98–106. https://doi.org/10.1016/j.jhazmat.2017.09.028

    Article  CAS  PubMed  Google Scholar 

  10. Chen SX, Zhang SS, A RH, Han YF, (2020) A new rhodamine probe with large stokes shift for Hg2+ detection and its application in real sample analysis. Tetrahedron Letters 61(27):152077. https://doi.org/10.1016/j.tetlet.2020.152077

    Article  CAS  Google Scholar 

  11. Yuan ZH, Yang YS, Lv PC, Zhu HL (2020) Recent progress in small-molecule fluorescent probes for detecting mercury ions. Crit Rev Anal Chem. https://doi.org/10.1080/10408347.2020.1797466

  12. Petdum A, Panchan W, Sirirak J, Promarak V, Sooksimuang T, Wanichacheva N (2018) Colorimetric and fluorescent sensing of a new FRET system via [5] helicene and rhodamine 6G for Hg2+ detection. New J Chem 42:1396–1402. https://doi.org/10.1039/c7nj04129b

  13. Lee YH, Park N, Park YB, Hwang YJ, Kang C, Kim JS (2014) Organelle-selective fluorescent Cu2+ ion probes: revealing the endoplasmic reticulum as a reservoir for Cu-overloading. Chemical Communications 50:3197–3200. https://doi.org/10.1039/c4cc00091a

    Article  CAS  PubMed  Google Scholar 

  14. Wu XF, Ma QJ, Wei XJ, Hou YM, Zhu X (2013) A selective fluorescent sensor for Hg2+ based on covalently immobilized naphthalimide derivative. Sensors and Actuators B: Chemical 183:565–573. https://doi.org/10.1016/j.snb.2013.04.024

    Article  CAS  Google Scholar 

  15. Song F, Yang C, Shao XT, Du L, Zhu J, Kan C (2019) A reversible “turn-off-on” fluorescent probe for real-time visualization of mercury(II) in environmental samples and its biological applications. Dyes Pigm 165:444–450. https://doi.org/10.1016/j.dyepig.2019.02.054

  16. Wang QM, Jin L, Wang WL, Hu TX, Chen C (2019) Rhodamine derivatives as selective “naked-eye” colorimetric and fluorescence off-on sensor for Hg2+ in aqueous solution and its applications in bioimaging. J Lumin 209:411–419. https://doi.org/10.1016/j.jlumin.2019.02.024

  17. Zhang XF, Wang TR, Cao XQ, Shen SL (2020) A near-infrared rhodamine-based lysosomal pH probe and its application in lysosomal pH rise during heat shock. Spectrochim Acta Part A Mol Biomol Spectrosc 227:117761 https://doi.org/10.1016/j.saa.2019.117761

  18. Das S, Rissanen K, Sahoo P (2019) Rare crystal structure of open spirolactam ring along with the closed-ring form of a rhodamine derivative: Sensing of Cu2+ Ions from Spinach. American Chemical Society Omega, 4:5270–5274. https://doi.org/10.1021/acsomega.9b00053

  19. Bao XF, Shi JX, Nie XM, Zhou BJ, Wang XL, Zhang LY, Liao H, Pang T (2014) A new Rhodamine B-based “on-off” chemical sensor with high selectivity and sensitivity toward Fe3+ and its imaging in living cells. Bioorganic and Medicinal Chemistry 22:4826–4835. https://doi.org/10.1016/j.bmc.2014.06.054

    Article  CAS  PubMed  Google Scholar 

  20. Kan C, Song F, Shao XT, Wu LY, Zhu J (2020) Fe (III) induced fluorescent probe based on triamine and rhodamine derivatives and its applications in biological imaging. J Photochem Photobiol A: Chem 390:112306. https://doi.org/10.1016/j.jphotochem.2019.112306

  21. Huang K, Yue YX, Jiao XJ, Liu C, Wang Q, He S, Zhao LC, Zeng XS (2017) Fluorescence regulation of 4-aminobenzofluoran and its applications for Cu2+-selective fluorescent probe and bioimaging. Dyes Pigm 143:379–386. https://doi.org/10.1016/j.dyepig.2017.04.064

  22. Qiao B, Sun SG, Jiang N, Zhang S, Peng XJ (2014) A ratiometric fluorescent probe for determining Pd2+ ions based on coordination. Dalton Transactions 43:4626–4630. https://doi.org/10.1039/c3dt53541j

    Article  CAS  PubMed  Google Scholar 

  23. Aich K, Goswami S, Das S, Mukhopadhyay CD, Quah CK, Fun HK (2015) Cd2+ triggered the FRET “ON”: A new molecular switch for the ratiometric detection of Cd2+ with live-cell imaging and bound X-ray structure. Inorg Chem 54:7309–7315. https://doi.org/10.1021/acs.inorgchem.5b00784

    Article  CAS  PubMed  Google Scholar 

  24. Tang JL, Li CY, Li YF, Lu X, Qi HR (2015) A highly sensitive and selective fluorescent probe for trivalent aluminum ion based on rhodamine derivative in living cells. Anal Chim Acta 888:155–161. https://doi.org/10.1016/j.aca.2015.07.033

    Article  CAS  Google Scholar 

  25. Wu GW, Wang ZY, Zhang WX, Chen W, Jin XX, Lu HF (2019) A novel rhodamine B and purine derivative-based fluorescent chemosensor for detection of palladium. Inorganic Chemistry Communications 102:233–239. https://doi.org/10.1016/j.inoche.2019.02.038

    Article  CAS  Google Scholar 

  26. Li G, Liu G, Zhang DB, Pu SZ (2016) A new fluorescence probe based on fluorescein-diarylethene fluorescence resonance energy transfer system for rapid detection of Cd2+. Tetrahedron 72:6390–6396. https://doi.org/10.1016/j.tet.2016.08.037

    Article  CAS  Google Scholar 

  27. Wu ZY, Xu ZY, Tan HY, Li X, Yan JW, Dong CZ, Zhang L (2019) Two novel rhodamine-based fluorescent probes for the rapid and sensitive detection of Fe3+: Experimental and DFT calculations. Spectrochimica Acta Part A: Molecular Biomolecular Spectroscopy 213:167–175. https://doi.org/10.1016/j.saa.2019.01.032

    Article  CAS  Google Scholar 

  28. Shree GJ, Sivaraman G, Siva A, Chellappa D (2019) Anthracene- and pyrene-bearing imidazoles as turn-on fluorescent chemosensor for aluminum ion in living cells. Dyes and Pigments 163:204–212. https://doi.org/10.1016/j.dyepig.2018.11.061

    Article  CAS  Google Scholar 

  29. Tang TG, Guo WB, Zhang YP, Xu DM (2019) A novel 1, 8-naphthalimide-based "turn-on" fluorescent sensor for Fe3+. J Fluoresc 29:445–450. https://doi.org/10.1007/s10895-019-02354-8

  30. Cao XR, Zhang FF, Bai YJ, Ding XH, Sun W (2019) A highly selective “turn-on” fluorescent probe for detection of Fe3+ in cells. J Fluoresc 29:425–434. https://doi.org/10.1007/s10895-019-02351-x

    Article  CAS  PubMed  Google Scholar 

  31. Song F, Yang C, Liu HB, Gao ZG, Zhu J, Bao XF, Kan C (2019) Dual-binding pyridine and rhodamine B conjugate derivatives as fluorescent chemosensors for ferric ions in aqueous media and living cells. Analyst 144:3094–3102. https://doi.org/10.1039/c8an01915k

    Article  CAS  PubMed  Google Scholar 

  32. Bozkurt E, Gul HI (2018) A novel pyrazoline-based fluorometric “Turn-off” sensing for Hg2+. Sensor Actuat B-Chem 255:814–825. https://doi.org/10.1016/j.snb.2017.08.062

  33. Wang Y, Ding H, Wang S, Fan C, Tu Y, Liu G, Pu S (2019) A ratiometric and colorimetric probe for detecting Hg2+ based on naphthalimide–rhodamine and its staining function in cell imaging. RSC Advances 9:11664–11669. https://doi.org/10.1039/c9ra01459d

    Article  CAS  Google Scholar 

  34. Manoj K, Naresh K, Vandana B (2011) Naphthalimide appended rhodamine derivative: Through bond energy transfer for sensing of Hg2+ ions. Org Lett 13(6):1422–1425. https://doi.org/10.1021/ol2001073

    Article  CAS  Google Scholar 

  35. Orriach-Fernández FJ, Medina-Castillo A, Fernández-Sánchez JF et al (2013) Hg2+-selective sensing film based on the incorporation of a rhodamine 6G derivative into a novel hydrophilic water-insoluble copolymer. Anal Methods 5:6642–6648. https://doi.org/10.1039/c3ay40717a

  36. Chereddy NR, Saranraj K, Barui AK, Patra CR, Rao VJ, Thennarasu S (2014) Donor atom selective coordination of Fe3+ and Cr3+ trigger fluorophore specific emission in a rhodamine-naphthalimide dyad. RSC Advances 4:24324–24327. https://doi.org/10.1039/c4ra02797c

  37. Goswami S, Das S, Aich K, Sarkar D, Mondal TK, Quah CK, Fun HK (2013) CHEF induced highly selective and sensitive turn-on fluorogenic and colorimetric sensor for Fe3+. Dalton Transactions 42:15113–15119. https://doi.org/10.1039/c3dt51974k

    Article  CAS  PubMed  Google Scholar 

  38. Huang L, Hou FP, Cheng J, Xi PX, Chen FJ, Bai DC, Zeng ZZ (2012) Selective off-on fluorescent chemosensor for detection of Fe3+ ions in aqueous media. Organic and Biomolecular Chemistry 10:9634–9638. https://doi.org/10.1039/c2ob26258d

    Article  CAS  PubMed  Google Scholar 

  39. Sunnapu O, Kotla NG, Maddiboyina B, Singaravadivel S, Sivaraman G (2016) A rhodamine based “turn-on” fluorescent probe for Pb (II) and live cell imaging. RSC Advances 6:656–660. https://doi.org/10.1039/c5ra20482h

    Article  CAS  Google Scholar 

  40. Zhou LY, Wang QQ, Zhang XB, Tan WH (2015) Through-bond energy transfer-based ratiometric two-photon probe for fluorescent imaging of Pd2+ ions in living cells and tissues. Analytical Chemistry 87:4503–4507. https://doi.org/10.1021/acs.analchem.5b00505

    Article  CAS  PubMed  Google Scholar 

  41. Wang M, Liu XM, Lu HZ, Wang HM, Qin ZH (2015) Highly selective and reversible chemosensor for Pd2+ detected by fluorescence, colorimetry, and test paper. ACS Applied Materials and Interfaces 7:1284–1289. https://doi.org/10.1021/am507479m

    Article  CAS  PubMed  Google Scholar 

  42. Zeng RF, Lan JS, Wu T, Liu L, Liu Y, Ho RJY, Ding Y, Zhang T (2020) A novel mitochondria-targetted near-infrared fluorescent probe for selective and colorimetric detection of sulfite and its application in vitro and vivo. Food Chemistry 318:126358. https://doi.org/10.1016/j.foodchem.2020.126358

    Article  CAS  PubMed  Google Scholar 

  43. Li M, Jiang XJ, Wu HH, Lu HL, Li HY, Xu H, Zang SQ, Mak TC (2015) A dual functional probe for “turn-on” fluorescence response of Pb2+ and colorimetric detection of Cu2+ based on a rhodamine derivative in aqueous media. Dalton Transactions 44:17326–17334. https://doi.org/10.1039/c5dt02731d

    Article  CAS  PubMed  Google Scholar 

  44. Zhao H, Ding HC, Kang HM, Fan CB, Liu G, Pu SZ (2019) A solvent-dependent chemosensor for fluorimetric detection of Hg2+ and colorimetric detection of Cu2+ based on a new diarylethene with a rhodamine B unit. RSC Advances 9:42155–42162. https://doi.org/10.1039/c9ra08557b

    Article  CAS  Google Scholar 

  45. Wang S, Ding HC, Wang YS, Fan CB, Liu G, Pu SZ (2019) Novel multi-responsive fluorescence switch for Hg2+ and UV/visible lights based on diarylethene-rhodamine derivative. Tetrahedron 75:1517–1524. https://doi.org/10.1016/j.tet.2019.01.071

    Article  CAS  Google Scholar 

  46. Xu HT, Ding HC, Li G, Fan CB, Liu G, Pu SZ (2017) A highly selective fluorescent chemosensor for Fe3+ based on a new diarylethene with a rhodamine 6G unit. RSC Advances 7:29827–29834. https://doi.org/10.1039/c7ra04728b

    Article  CAS  Google Scholar 

  47. Sun Y, Dong B, Lu Y, Song W, Mehmood AH, Lin W (2020) A sensitive and selective fluorescent probe for the detection of endogenous peroxynitrite (ONOO-) in living cells. Analytical Methods 12:2841–2845. https://doi.org/10.1039/d0ay00012d

    Article  CAS  PubMed  Google Scholar 

  48. Wang L, Ren MG, Li ZH, Dai LX, Lin WY (2019) Development of a FRET-based ratiometric fluorescent probe to monitor the changes in palladium(ii) in aqueous solution and living cells. New Journal of Chemistry 43:552–555. https://doi.org/10.1039/c8nj04866e

    Article  CAS  Google Scholar 

  49. Guo SL, Liu G, Fan CB, Pu SZ (2018) A new diarylethene-derived probe for colorimetric sensing of Cu(II) and fluorometric sensing of Cu(II) and Zn(II): Photochromism and High Selectivity. Sensor Act B-Chem. 266:603–613. https://doi.org/10.1016/j.snb.2018.03.168

  50. Shi F, Cui SQ, Liu HL, Pu SZ (2020) A high selective fluorescent sensor for Cu2+ in solution and test paper strips. Dyes and Pigments 173:107914. https://doi.org/10.1016/j.dyepig.2019.107914

    Article  CAS  Google Scholar 

  51. Qiu SY, Lu MM, Cui SQ, Wang Z, Pu SZ (2019) A bifunctional sensor based on diarylethene for the colorimetric recognition of Cu2+ and fluorescence detection of Cd2+. RSC Advances 9:29141–29148. https://doi.org/10.1039/c9ra04965g

    Article  CAS  Google Scholar 

  52. Wang Z, Cui SQ, Qiu SY, Pu SZ (2018) A highly selective fluorescence “turn-on” sensor for Ca2+ based on diarylethene with a triazozoyl hydrazine unit. RSC Advances 8:29295–29300. https://doi.org/10.1039/c8ra06039h

    Article  CAS  Google Scholar 

  53. Pu SZ, Tong ZP, Liu G, Wang RJ (2013) Multi-addressable molecular switches based on a new diarylethene salicylal Schiff base derivative. Journal of Materials Chemistry C 1(31):4726–4739. https://doi.org/10.1039/c3tc30804a

    Article  CAS  Google Scholar 

  54. Liu YM, Shen R, Ru JX, Yao X, Yang Y, Liu HL, Tang XL, Bai DC, Zhang GL, Liu WS (2016) A reversible rhodamine 6G-based fluorescence turn-on probe for Fe3+ in water and its application in living cell imaging. RSC Advances 6:111754–111759. https://doi.org/10.1039/c5ra09758d

    Article  CAS  Google Scholar 

  55. Zhang YR, Zhao ZM, Su L, Miao JY, Zhao BX (2016) A ratiometric fluorescence sensor for HOCl based on a FRET platform and application in living cells. RSC Advances 6:17059–17063. https://doi.org/10.1039/c5ra26027b

    Article  CAS  Google Scholar 

  56. Jiao XY, Xiao YS, Li Y, Liang MW, Xie XL, Wang X, Tang B (2018) Evaluating drug-induced liver injury and its remission via discrimination and imaging of HClO- and H2S with a two-photon fluorescent probe. Anal Chem 90:7510–7516. https://doi.org/10.1021/acs.analchem.8b01106

    Article  CAS  PubMed  Google Scholar 

  57. Adhikari S, Ta S, Ghosh A, Guria S, Pal A, Ahir M, Adhikary A, Hira SK, Manna PP, Das D (2019) A 1,8 Naphthalimide anchor rhodamine B based FRET probe for ratiometric detection of Cr3+ ion in living cells. Journal of Photochemistry and Photobiology A: Chemistry 372:49–58. https://doi.org/10.1016/j.jphotochem.2018.12.010

    Article  CAS  Google Scholar 

  58. Biswal B, Bag B (2013) Preferences of rhodamine coupled (aminoalkyl)-piperazine probes towards Hg (II) ion and their FRET mediated signaling. Organic and Biomolecular Chemistry 11:4975–4992. https://doi.org/10.1039/c3ob40648b

    Article  CAS  PubMed  Google Scholar 

  59. Li YJ, Pan WH, Zheng CH, Pu SZ (2020) A diarylethene derived Fe3+ fluorescent chemosensor and its application in wastewater analysis. Journal of Photochemistry and Photobiology A: Chemistry 389:112282. https://doi.org/10.1016/j.jphotochem.2019.112282

    Article  CAS  Google Scholar 

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Acknowledgements

The author was very appreciation for the support of the National Natural Science Foundation of China (41867052, 21662015, 21861017, 1867053), the Science Funds of the Education Office of Jiangxi, China (GJJ190613), and the Masters' Innovative Foundation of Jiangxi Science and Technology Normal University (YC2019-X09).

Funding

This work was supported by the National Natural Science Foundation of China (Grant numbers [41867052, 21662015, 21861017, 1867053]), the Science Funds of the Education Office of Jiangxi, China (Grant numbers [GJJ190613], and the Masters' Innovative Foundation of Jiangxi Science and Technology Normal University (Grant numbers [YC2019-X09]).

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  1. Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang, 330013, PR China

    Xiumei Li, Xue Li, Heng Zhao, Huimin Kang, Congbin Fan, Gang Liu & Shouzhi Pu

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  2. Xue Li
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Contributions

Material preparation, data collection and analysis were performed by Xiumei Li, Heng Zhao and Huimin Kang; the first draft of the manuscript was written by Xiumei Li and revised by Xue Li and Congbin Fan; Gang Liu and Shouzhi Pu gave guidance ideas and experimental platform.

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Correspondence to Gang Liu or Shouzhi Pu.

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Li, X., Li, X., Zhao, H. et al. A Novel Diarylethene-rhodamine Unit Based Chemosensor for Fluorimetric and Colorimetric Detection of Hg2+. J Fluoresc 31, 1513–1523 (2021). https://doi.org/10.1007/s10895-021-02775-4

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