A Novel Turn-On Fluorescent Probe Based on Naphthalimide for Highly Selective and Sensitive Detection of Hydrogen Sulfide in Solution and Gas

doi:10.6023/cjoc202305002

Abstract

A novel turn-on fluorescent probe (NPHQ) based on naphthalimide had been constructed to detect hydrogen sulfide. The nucleophilic effect of hydrogen sulfide induced the decomposition of naphthoquinone structure, which resulted in the disappearance of photo-induced electron transfer (PET) of NPHQ and recovery of intramolecular charge transfer (ICT) of naphthalimide. The fluorescence intensities of NPHQ showed a linear enhancement response to hydrogen sulfide in the concentration range of 0~0.5 μmol/L with limit of detection of 1.68 nmol/L. Moreover, NPHQ held promising application prospects for detecting hydrogen sulfide in solution and gas based on its high selectivity, sensitivity and specific turn-on emission.

Key words: hydrogen sulfide, fluorescence probe, turn-on, naphthalimide, solution and gas

Cite this article

Wu Zhou, Min Peng, Qingxiang Liang, Aibin Wu, Wenming Shu, Weichu Yu. A Novel Turn-On Fluorescent Probe Based on Naphthalimide for Highly Selective and Sensitive Detection of Hydrogen Sulfide in Solution and Gas[J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4277-4283.

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Fig. & Tab. 6

Scheme 1. Synthetic route of NPHQ

Figure 1. Fluorescence response of NPHQ (10 μmol/L) against different interfering analytes (100 μmol/L)

Figure 2. (a) Absorption and emission spectra of NPHQ (10 μmol/L) in DMSO/H2O (V/V=1/9) solution in absence and presence of H2S (100 μmol/L) (inset: the fluorescence color of NPHQ in absence and presence of H2S under 365 nm fluorescent lamp); (b) fluorescence intensity changes of NPHQ (10 μmol/L) in DMSO/H2O (V/V=1/9) solution with the addition of H2S (0~0.5 μmol/L) (inset: linear relationship between the fluorescence intensity of NPHQ and the concentration of H2S)

Figure 3. Fluorescence intensities of NPHQ (10 μmol/L) in the presence of 100 μmol/L interfering species including H2S, Mn2+, Al3+, Sn4+, K+, Cr3+, Ca2+, Zn2+, Na+, Ba2+, Ce3+, Mg2+, I–, ${{\text{S}}_{2}}\text{O}_{5}^{2-}$, $\text{HCO}_{3}^{-}$, $\text{MnO}_{\text{4}}^{-}$, $\text{HSO}_{3}^{-}$, $\text{SO}_{\text{4}}^{2-}$, $\text{C}{{\text{r}}_{2}}\text{O}_{7}^{2-}$, H2- $\text{PO}_{4}^{-}$, $\text{CO}_{3}^{2-}$, Br–, $\text{ClO}_{3}^{-}$, $\text{NO}_{2}^{-}$, ClO–, H2O2, GSH, Cys, Hcy, DTT and βME (λex=390 nm)

Figure 4. Proposed recognition mechanism of NPHQ to H2S

Figure 5. Test strips for detection of H2S gas (0, 38, 76, 152, 228, 301, 455, 607 mg/m3 ) under fluorescent lamp λex=365 nm. Pictures were taken after exposure to H2S gas for 10 s

References 33

[1]	(a) Zhang X.; Bian J. S. ACS Chem. Neurosci. 2014, 5, 876. doi: 10.1021/cn500185g
	(b) Chen C. Q.; Xin H.; Zhu Y. Z. Acta Pharmacol. Sin. 2007, 28, 1709. doi: 10.1111/j.1745-7254.2007.00629.x
	(c) Panthi S.; Manandhar S.; Gautam K. Transl. Neurodegener. 2018, 7, 1. doi: 10.1186/s40035-018-0106-z
	(d) Li W.; Wang L.; Yin S.; Lai H.; Yuan L.; Zhang X. Chem. Sci. 2020, 11, 7991. doi: 10.1039/D0SC03336G
[2]	(a) Polhemus D. J.; Lefer D. J. Circ. Res. 2014, 114, 730. doi: 10.1161/CIRCRESAHA.114.300505 pmid: 24526678
	(b) Yang M.; Fan J.; Du J.; Peng X. Chem. Sci. 2020, 11, 5127. doi: 10.1039/D0SC01482F pmid: 24526678
[3]	Wu L.; Wang R. Pharmacol. Rev. 2005, 57, 585. doi: 10.1124/pr.57.4.3
[4]	Lamattina L.; Garcia-Mata C.; Graziano M.; Pagnussat G. Annu. Rev. Plant Biol. 2003, 54, 109. pmid: 14502987
[5]	(a) Cirino G.; Szabo C.; Papapetropoulos A. Physiol. Rev. 2023, 103, 31. doi: 10.1152/physrev.00028.2021
	(b) Szabo C. Nat. Rev. Drug Discovery 2007, 6, 917. doi: 10.1038/nrd2425
[6]	Whiteman M.; Winyard P. G. Expert. Rev. Clin. Pharmacol. 2011, 4, 13. doi: 10.1586/ecp.10.134
[7]	Li Y.; Bai J.; Yang Y. H.; Hoshi N.; Chen D. B. Antioxidants 2020, 9. 1127. doi: 10.3390/antiox9111127
[8]	Kimura H. Antioxid. Redox Signaling 2010, 12, 1111. doi: 10.1089/ars.2009.2919
[9]	Hu X.; Chi Q.; Wang D.; Chi X.; Teng X.; Li S. Ecotoxicol. Environ. Saf. 2018, 164, 201. doi: 10.1016/j.ecoenv.2018.08.029
[10]	Feliers D.; Lee H. J.; Kasinath B. S. Antioxid. Redox Signaling 2016, 25, 720. doi: 10.1089/ars.2015.6596
[11]	Munaron L.; Avanzato D.; Moccia F.; Mancardi D. Cell Calcium. 2013, 53, 77. doi: 10.1016/j.ceca.2012.07.001 pmid: 22840338
[12]	Roorda M.; Miljkovic J. L.; van Goor H.; Henning R. H.; Bouma H. R. Redox Biol. 2021, 43, 101961. doi: 10.1016/j.redox.2021.101961
[13]	(a) Elrod J. W.; Calvert J. W.; Morrison J.; Doeller J. E.; Kraus D. W.; Tao L.; Jiao X.; Scalia R.; Kiss L.; Szabo C.; Kimura H.; Chow C. W.; Lefer D. J. Proc. Natl. Acad. Sci. 2007, 104, 15560. doi: 10.1073/pnas.0705891104
	(b) Yang G.; Wu L.; Jiang B.; Yang W.; Qi J.; Cao K.; Meng Q.; Mustafa A. K.; Mu W.; Zhang S.; Snyder S. H.; Wang R. Science 2008, 322, 587. doi: 10.1126/science.1162667
	(c) Linden D. R. Antioxid. Redox Signaling 2014, 20, 818. doi: 10.1089/ars.2013.5312
	(d) Olson K. R.; Donald J. A. Acta Histochem. 2009, 111, 244. doi: 10.1016/j.acthis.2008.11.004
	(e) Bhatia M.; Gaddam R. R. Antioxid. Redox Signaling 2021, 34, 1368. doi: 10.1089/ars.2020.8211
	(f) Dilek N.; Papapetropoulos A.; Toli-ver-Kinsky T.; Szabo C. Pharmacol. Res. 2020, 161, 105119. doi: 10.1016/j.phrs.2020.105119
[14]	Petruci J. F.; Fortes P. R.; Kokoric V.; Wilk A.; Raimundo I. M. Jr.; Cardoso A. A.; Mizaikoff B. Analyst 2014, 139, 198. doi: 10.1039/C3AN01793A
[15]	Choi M. G.; Cha S.; Lee H.; Jeon H. L.; Chang S. K. Chem. Commun. 2009, 47, 7390.
[16]	(a) Hammers M. D.; Taormina M. J.; Cerda M. M.; Montoya L. A.; Seidenkranz D. T.; Parthasarathy R.; Pluth M. D. J. Am. Chem. Soc. 2015, 137, 10216. doi: 10.1021/jacs.5b04196
	(b) Lv J.; Wang F.; Qiang J.; Ren X.; Chen Y.; Zhang Z.; Wang Y.; Zhang W.; Chen X. Biosens. Bioelectron. 2017, 87, 96. doi: 10.1016/j.bios.2016.08.018
	(c) Jin X.; Wu S.; She M.; Jia Y.; Hao L.; Yin B.; Wang L.; Obst M.; Shen Y.; Zhang Y.; Li J. Anal. Chem. 2016, 88, 11253. doi: 10.1021/acs.analchem.6b04087
	(d) Wang H.; Yang D.; Tan R.; Zhou Z. J.; Xu R.; Zhang J. F.; Zhou Y. Sens. Actuators, B 2017, 247, 883. doi: 10.1016/j.snb.2017.03.030
[17]	Raymond D. M.; Nilsson B. L. Chem. Soc. Rev. 2018, 47, 3659. doi: 10.1039/C8CS00115D
[18]	Gun J.; Modestov A. D.; Kamyshny A.; Ryzkov D.; Gitis V.; Goifman A.; Lev O.; Hultsch V.; Grischek T.; Worch E. Microchim. Acta 2004, 146, 229. doi: 10.1007/s00604-004-0179-5
[19]	(a) Wang R.; Gu X.; Li Q.; Gao J.; Shi B.; Xu G.; Zhu T.; Tian H.; Zhao C. J. Am. Chem. Soc. 2020, 142, 15084. doi: 10.1021/jacs.0c06533
	(b) Qian Y.; Karpus J.; Kabil O.; Zhang S. Y.; Zhu H. L.; Banerjee R.; Zhao J.; He C. Nat. Commun. 2011, 2, 495. doi: 10.1038/ncomms1506
[20]	(a) Chen Z.; Mu X.; Han Z.; Yang S.; Zhang C.; Guo Z.; Bai Y.; He W. J. Am. Chem. Soc. 2019, 141, 17973. doi: 10.1021/jacs.9b09181
	(b) Ge C.; Di X.; Han S.; Wang M.; Qian X.; Su Z.; Liu H. K.; Qian Y. Chem. Commun. 2021, 57, 1931. doi: 10.1039/D0CC07982K
	(c) Teng Y.; Yang H.; Li X.; Wang Y. C.; Yin D. L.; Tian Y. L. Chin. J. Chem. 2022, 40, 209. doi: 10.1002/cjoc.v40.2
[21]	Wan Q.; Song Y.; Li Z.; Gao X.; Ma H. Chem. Commun. 2013, 49, 502. doi: 10.1039/C2CC37725J
[22]	(a) Xuan W.; Pan R.; Cao Y.; Liu K.; Wang W. Chem. Commun. 2012, 48, 10669. doi: 10.1039/c2cc35602c
	(b) Liu C.; Pan J.; Li S.; Zhao Y.; Wu L. Y.; Berkman C. E.; Whorton A. R.; Xian M. Angew. Chem., Int. Ed. 2011, 50, 10327. doi: 10.1002/anie.v50.44
[23]	(a) An Y.; Wang P.; Yue Z. Spectrochim. Acta, Part A 2019, 216, 319. doi: 10.1016/j.saa.2019.03.065
	(b) Sun M.; Yu H.; Li H.; Xu H.; Huang D.; Wang S. Inorg. Chem. 2015, 54, 3766. doi: 10.1021/ic502888j
[24]	(a) Ren X.; Wang F.; Lv J.; Wei T.; Zhang W.; Wang Y.; Chen X. Dyes Pigm. 2016, 129, 156. doi: 10.1016/j.dyepig.2016.02.027
	(b) Li X.; Wang A.; Wang J.; Lu J. Anal. Chem. 2019, 91, 15703. doi: 10.1021/acs.analchem.9b03877
	(c) Hu Y.; Chen Z. H.; Ma L. L.; Zhang Z. Y.; Zhang H.; Yi F. P.; Liu C. X. Tetrahedron 2022, 117, 132837.
[25]	Peng B.; Zhang C.; Marutani E.; Pacheco A.; Chen W.; Ichinose F.; Xian M. Org. Lett. 2015, 17, 1541. doi: 10.1021/acs.orglett.5b00431 pmid: 25723840
[26]	Hong J.; Feng W.; Feng G. Sens. Actuators, B 2018, 262, 837. doi: 10.1016/j.snb.2018.02.070
[27]	(a) Kaushik R.; Ghosh A.; Singh A.; Jose D. A. Anal. Chim. Acta 2018, 1040, 177. doi: S0003-2670(18)30982-6 pmid: 30327108
	(b) Han H. H.; Tian H.; Zang Y.; Sedgwick A. C.; Li J.; Sessler J. L.; He X. P.; James T. D. Chem. Soc. Rev. 2021, 50, 9391. doi: 10.1039/D0CS01183E pmid: 30327108
[28]	(a) Geraghty C.; Wynne C.; Elmes R. B. P. Coord. Chem. Rev. 2021, 437, 213713. doi: 10.1016/j.ccr.2020.213713
	(b) Zhou W.; Liang Q. X.; Wu A. B.; Su W. M.; Yu W. C. J. Appl. Polym. Sci. 2023, 140, https://doi.org/10.1002/app.53727
	(c) Zhou W.; Chen Q.; Wu A. B.; Zhang Y.; Yu W. C. J. Chin. Chem. Soc. 2020, 67, 1213. doi: 10.1002/jccs.v67.7
	(d) Shi C. T.; Luo J.; Wang Y. C.; Ding L.; Liang Q.; Yang Z.; Lu J.; Wu A. B. Spectrochim. Acta, Part A 2023, 289, 122245. doi: 10.1016/j.saa.2022.122245
	(e) Shi C. T.; Yu M.; Wu A. B.; Luo J. X.; Li X. J.; Wang N. C.; Shu W. M.; Yu W. C. Chin. J. Org. Chem. 2022, 42, 2806. (in Chinese) doi: 10.6023/cjoc202204032
	(师春甜, 余美, 吴爱斌, 罗江雄, 黎小军, 王宁晨, 舒文明, 余维初, 有机化学, 2022, 42, 2806.) doi: 10.6023/cjoc202204032
	(f) Shi C. T.; Huang Z. Y.; Wu A. B.; Hu Y. X.; Wang N. C., Zhang Y.; Shu W. M.; Yu W. C. RSC Adv. 2021, 11, 29632. doi: 10.1039/D1RA05048F
	(g) Ren J. B.; Wang L.; Guo R.; Tang Y. H.; Zhou H. M.; Lin W. Y. Acta Chim. Sinica 2021, 79, 87. (in Chinese) doi: 10.6023/A20080399
	(任江波, 王蕾, 郭锐, 唐永和, 周红梅, 林伟英, 化学学报, 2021, 79, 87.) doi: 10.6023/A20080399
[29]	(a) Lee M. H.; Kim J. S.; Sessler J. L. Chem. Soc. Rev. 2015, 44, 4185. doi: 10.1039/C4CS00280F
	(b) Goswami S.; Sen D.; Das N. K. Org. Lett. 2010, 12, 856. doi: 10.1021/ol9029066
[30]	Yang L. L.; Tang A. L.; Wang P. Y.; Yang S. Org. Lett. 2020, 22, 8234. doi: 10.1021/acs.orglett.0c02814
[31]	(a) Ma T.; Huo F.; Wen Y.; Glass T. E.; Yin C. Spectrochim. Acta, Part A 2019, 214, 355. doi: 10.1016/j.saa.2019.02.073
	(b) Zhang J.; Mu S.; Wang Y.; Li S.; Shi X.; Liu X.; Zhang H. Anal. Chim. Acta 2022, 1195, 339457. doi: 10.1016/j.aca.2022.339457
	(c) Ou L.; Guo R.; Lin W. Anal. Methods 2021, 13, 1511. doi: 10.1039/D1AY00097G
	(d) Zhang C.; Zhang L.; Li Y.; Ren Z.; Li L.; Zhang Y.; Li Y.; Liu C. J. Mol. Struct. 2022, 1250, 131777. doi: 10.1016/j.molstruc.2021.131777
	(e) Guo M. Y.; Wang W.; Ainiwaer D.; Yang Y. S.; Wang B. Z.; Yang J.; Zhu H. L. Talanta 2022, 237, 122960. doi: 10.1016/j.talanta.2021.122960
	(f) Du Y.; Wang H.; Zhang T.; Wen W.; Li Z.; Bi M.; Liu J. Spectrochim. Acta, Part A 2022, 265, 120390. doi: 10.1016/j.saa.2021.120390
[32]	Choi M. G.; Kim N. Y.; Lee Y. J.; Ahn S.; Chang S. K. Chem. Commun. 2019, 55, 11398. doi: 10.1039/C9CC05597E
[33]	Shi J.; Wang Y.; Tang X.; Liu W.; Jiang H.; Dou W.; Liu W. Dyes Pigm. 2014, 100, 255. doi: 10.1016/j.dyepig.2013.09.021

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