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A Smart Fluorescent Probe Based on Salicylaldehyde Schiff’s Base with AIE and ESIPT Characteristics for the Detections of N2H4 and ClO

  • Ya Xie
  • Liqiang YanEmail author
  • Yujian Tang
  • Minghui Tang
  • Shaoyang Wang
  • Li Bi
  • Wanying Sun
  • Jianping Li
ORIGINAL ARTICLE
  • 42 Downloads

Abstract

Smart and versatile salicylaldehyde Schiff’s bases have been proved their excellent performances including large shocks shift, dual emission wavelengths and sensitive to environment for fluorescence analysis. Herein, a simple salicylaldehyde Schiff’s base molecular (PBAS) with aggregation-induced emission (AIE) and the excited-state intramolecular proton-transfer (ESIPT) effects was constructed for detecting N2H4 and ClO. The highly specific and sensitive response to N2H4 was witnessed by the fast turn-on of the strong blue fluorescence and to ClO was observed by the rapid turn off of the weak green fluorescence simultaneous decomposing of the probe. The results of mass spectrum analysis showed that probe PBAS decomposed under the influence of N2H4, whereas probe PBAS can complex with ClO and prevent effective ESIPT process. Benefiting from its high properties, this fluorescence molecular provides an effective tool for probing N2H4 and ClO in live cells.

Keywords

Fluorescence probe N2H4 ClO Salicylaldehyde Schiff’s bases 

Notes

Acknowledgements

This work was supported by College students’ innovation and entrepreneurship training program (201810596130), the Natural Science Foundation of Guangxi Province of China (Project No.2015GXNSFFA139005) and High Level Innovation Teams of Guangxi Colleges & Universities and Outstanding Scholars Program (Guijiaoren [2014]49).

Supplementary material

10895_2019_2348_MOESM1_ESM.doc (2.6 mb)
ESM 1 (DOC 2661 kb)

References

  1. 1.
    Muzalevskiy VM, Rulev AY, Romanov AR, Kondrashov EV, Ushakov IA, Chertkov VA, Nenajdenko VG (2017) Selective, metal-free approach to 3-or 5-CF3-Pyrazoles: solvent switchable reaction of CF3-Ynones with Hydrazines. J Organomet Chem 82(14):7200–7214.  https://doi.org/10.1021/acs.joc.7b00774 Google Scholar
  2. 2.
    Tafreshi SS, Roldan A, de Leeuw NH (2017) Micro-kinetic simulations of the catalytic decomposition of hydrazine on the cu(111) surface. Faraday Discuss 197:41–57.  https://doi.org/10.1039/c6fd00186f Google Scholar
  3. 3.
    Serov A, Kwak C (2010) Direct hydrazine fuel cells: a review. Appl Catal B-Environ 98(1–2):1–9.  https://doi.org/10.1016/j.apcatb.2010.05.005 Google Scholar
  4. 4.
    Ragnarsson U (2001) Synthetic methodology for alkyl substituted hydrazines. Chem Soc Rev 30(4):205–213.  https://doi.org/10.1039/B010091a Google Scholar
  5. 5.
    Balsamo A, Macchia B, Macchia F, Rossello A, Giani R, Pifferi G, Pinza M, Broccali G (1983) Synthesis and antibacterial activities of new (alpha-hydrazinobenzyl)cephalosporins. J Med Chem 26(11):1648–1650Google Scholar
  6. 6.
    Ccorahua R, Troncoso OP, Rodriguez S, Lopez D, Torres FG (2017) Hydrazine treatment improves conductivity of bacterial cellulose/graphene nanocomposites obtained by a novel processing method. Carbohydr Polym 171:68–76.  https://doi.org/10.1016/j.carbpol.2017.05.005 Google Scholar
  7. 7.
    Jana MK, Gupta U, Rao CNR (2016) Hydrazine as a hydrogen carrier in the photocatalytic generation of H-2 using CdS quantum dots. Dalton T 45(38):15137–15141.  https://doi.org/10.1039/c6dt02505f Google Scholar
  8. 8.
    Kerai MDJ, Timbrell JA (1997) Effect of fructose on the biochemical toxicity of hydrazine in isolated rat hepatocytes. Toxicology 120(3):221–230.  https://doi.org/10.1016/S0300-483x(97)00059-0 Google Scholar
  9. 9.
    Waterfield CJ, Turton JA, Scales MDC, Timbrell JA (1993) Investigations into the effects of various hepatotoxic compounds on urinary and liver taurine levels in rats. Arch Toxicol 67(4):244–254.  https://doi.org/10.1007/Bf01974343 Google Scholar
  10. 10.
    Garrod S, Bollard ME, Nichollst AW, Connor SC, Connelly J, Nicholson JK et al (2005) Integrated metabonomic analysis of the multiorgan effects of hydrazine toxicity in the rat. Chem Res Toxicol 18(2):115–122.  https://doi.org/10.1021/tx0498915 Google Scholar
  11. 11.
    Dickinson BC, Huynh C, Chang CJ (2010) A palette of fluorescent probes with varying emission colors for imaging hydrogen peroxide signaling in living cells. J Am Chem Soc 132(16):5906–5915.  https://doi.org/10.1021/ja1014103 Google Scholar
  12. 12.
    Yue YK, Huo FJ, Yin CX, Escobedo JO, Strongin RM (2016) Recent progress in chromogenic and fluorogenic chemosensors for hypochlorous acid. Analyst 141(6):1859–1873.  https://doi.org/10.1039/c6an00158k Google Scholar
  13. 13.
    Yap YW, Whiteman M, Cheung NS (2007) Chlorinative stress: An under appreciated mediator of neurodegeneration? Cell Signal 19(2):219–228.  https://doi.org/10.1016/j.cellsig.2006.06.013 Google Scholar
  14. 14.
    Pattison DI, Davies MJ (2006) Evidence for rapid inter- and intramolecular chlorine transfer reactions of histamine and carnosine chloramines: implications for the prevention of hypochlorous-acid-mediated damage. Biochemistry-Us 45(26):8152–8162.  https://doi.org/10.1021/bi060348s Google Scholar
  15. 15.
    Malle E, Buch T, Grone HJ (2003) Myeloperoxidase in kidney disease. Kidney Int 64(6):1956–1967.  https://doi.org/10.1046/j.1523-1755.2003.00336.x Google Scholar
  16. 16.
    Steinbeck MJ, Nesti LJ, Sharkey PF, Parvizi J (2006) Myeloperoxidase and chlorinated-peptides in osteoarthritis: potential biomarkers of the disease. J Bone Miner Res 21:S144–S144Google Scholar
  17. 17.
    Maruyama Y, Lindholm B, Stenvinkel P (2004) Inflammation and oxidative stress in ESRD - the role of myeloperoxidase\. J Nephrol 17:S72–S76Google Scholar
  18. 18.
    Sam CH, Lu HK (2009) The role of hypochlorous acid as one of the reactive oxygen species in periodontal disease. J Dent Sci 4(2):45–54.  https://doi.org/10.1016/S1991-7902(09)60008-8 Google Scholar
  19. 19.
    Yan LQ, Ma Y, Cui MF, Qi ZJ (2015) A novel coumarin-based fluorescence chemosensor containing L-histidine for aluminium(III) ions in aqueous solution. Anal Methods-Uk 7(15):6133–6138.  https://doi.org/10.1039/c5ay01466b Google Scholar
  20. 20.
    Thomas SW, Joly GD, Swager TM (2007) Chemical sensors based on amplifying fluorescent conjugated polymers. Chem Rev 107(4):1339–1386.  https://doi.org/10.1021/cr0501339 Google Scholar
  21. 21.
    Grimsdale AC, Chan KL, Martin RE, Jokisz PG, Holmes AB (2009) Synthesis of light-emitting conjugated polymers for applications in electroluminescent devices. Chem Rev 109(3):897–1091.  https://doi.org/10.1021/cr000013v Google Scholar
  22. 22.
    Luo JD, Xie ZL, Lam JWY, Cheng L, Chen HY, Qiu CF et al (2001) Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem Commun 18:1740–1741.  https://doi.org/10.1039/B105159h Google Scholar
  23. 23.
    Yuan WZ, Chen SM, Lam JWY, Deng CM, Lu P, Sung HHY, Williams ID, Kwok HS, Zhang Y, Tang BZ (2011) Towards high efficiency solid emitters with aggregation-induced emission and electron-transport characteristics. Chem Commun 47(40):11216–11218.  https://doi.org/10.1039/c1cc14122h Google Scholar
  24. 24.
    Zhao ZJ, Geng JL, Chang ZF, Chen SM, Deng CM, Jiang T, Qin W, Lam JWY, Kwok HS, Qiu H, Liu B, Tang BZ (2012) A tetraphenylethene-based red luminophor for an efficient non-doped electroluminescence device and cellular imaging. J Mater Chem 22(22):11018–11021.  https://doi.org/10.1039/c2jm31482g Google Scholar
  25. 25.
    Yan LQ, Li RJ, Shen W, Qi ZJ (2018) Multiple-color AIE coumarin-based Schiff bases and potential application in yellow OLEDs. J Lumin 194:151–155.  https://doi.org/10.1016/j.jlumin.2017.10.032 Google Scholar
  26. 26.
    Gui SL, Huang YY, Hu F, Jin YL, Zhang GX, Yan LS, Zhang D, Zhao R (2015) Fluorescence turn-on Chemosensor for highly selective and sensitive detection and bioimaging of Al3+ in living cells based on ion-induced aggregation. Anal Chem 87(3):1470–1474.  https://doi.org/10.1021/ac504153c Google Scholar
  27. 27.
    Zhao N, Gong Q, Zhang RX, Yang J, Huang ZY, Li N, Tang BZ (2015) A fluorescent probe with aggregation-induced emission characteristics for distinguishing homocysteine over cysteine and glutathione. J Mater Chem C 3(32):8397–8402.  https://doi.org/10.1039/c5tc01159k Google Scholar
  28. 28.
    Hong YN, Lam JWY, Tang BZ (2011) Aggregation-induced emission. Chem Soc Rev 40(11):5361–5388.  https://doi.org/10.1039/c1cs15113d Google Scholar
  29. 29.
    Mei J, Leung NLC, Kwok RTK, Lam JWY, Tang BZ (2015) Aggregation-induced emission: together we Shine, united we soar! Chem Rev 115(21):11718–11940.  https://doi.org/10.1021/acs.chemrev.5b00263 Google Scholar
  30. 30.
    Yan LQ, Qing TT, Li RJ, Wang ZW, Qi ZJ (2016) Synthesis and optical properties of aggregation-induced emission (AIE) molecules based on the ESIPT mechanism as pH- and Zn2+−responsive fluorescent sensors. RSC Adv 6(68):63874–63879.  https://doi.org/10.1039/c6ra09920c Google Scholar
  31. 31.
    Yan LQ, Kong ZN, Xia Y, Qi ZJ (2016) A novel coumarin-based red fluorogen with AIE, self-assembly, and TADF properties. New J Chem 40(8):7061–7067.  https://doi.org/10.1039/c6nj01296e Google Scholar
  32. 32.
    Padalkar VS, Seki S (2016) Excited-state intramolecular proton-transfer (ESIPT)-inspired solid state emitters. Chem Soc Rev 45(1):169–202.  https://doi.org/10.1039/c5cs00543d Google Scholar
  33. 33.
    Wang EJ, Lam JWY, Hu RR, Zhang C, Zhao YS, Tang B (2014) Twisted intramolecular charge transfer, aggregation-induced emission, supramolecular self-assembly and the optical waveguide of barbituric acid-functionalized tetraphenylethene. J Mater Chem C 2(10):1801–1807.  https://doi.org/10.1039/c3tc32161d Google Scholar
  34. 34.
    Yan LQ, Kong ZN, Shen W, Du WQ, Zhou Y, Qi ZJ (2016) An aggregation-induced emission (AIE) ratiometric fluorescent cysteine probe with an exceptionally large blue shift. RSC Adv 6(7):5636–5640.  https://doi.org/10.1039/c5ra22245a Google Scholar
  35. 35.
    An BK, Kwon SK, Jung SD, Park SY (2002) Enhanced emission and its switching in fluorescent organic nanoparticles. J Am Chem Soc 124(48):14410–14415.  https://doi.org/10.1021/ja0269082 Google Scholar
  36. 36.
    Kubo Y, Yamamoto M, Ikeda M, Takeuchi M, Shinkai S, Yamaguchi S, Tamao K (2003) A colorimetric and ratiometric fluorescent chemosensor with three emission changes: fluoride ion sensing by a triarylborane-porphyrin conjugate. Angew Chem Int Ed 42(18):2036–2040.  https://doi.org/10.1002/anie.200250788 Google Scholar
  37. 37.
    Zhang X, Yan YC, Hang YD, Wang J, Hua JL, Tian H (2017) A phenazine-barbituric acid based colorimetric and ratiometric near-infrared fluorescent probe for sensitively differentiating biothiols and its application in TiO2 sensor devices. Chem Commun 53(42):5760–5763.  https://doi.org/10.1039/c7cc01925d Google Scholar
  38. 38.
    Li XH, Zhang GX, Ma HM, Zhang DQ, Li J, Zhu DB (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(37):11543–11548.  https://doi.org/10.1021/ja0481530 Google Scholar
  39. 39.
    Koide Y, Urano Y, Hanaoka K, Terai T, Nagano T (2011) Development of an Si-rhodamine-based far-red to near-infrared fluorescence probe selective for Hypochlorous acid and its applications for biological imaging. J Am Chem Soc 133(15):5680–5682.  https://doi.org/10.1021/ja111470n Google Scholar
  40. 40.
    Ma Z, Sun W, Chen LZ, Li J, Liu ZZ, Bai HX, Zhu M, du L, Shi X, Li M (2013) A novel hydrazino-substituted naphthalimide-based fluorogenic probe for tert-butoxy radicals. Chem Commun 49(56):6295–6297.  https://doi.org/10.1039/c3cc42052c Google Scholar
  41. 41.
    Wu JS, Liu WM, Zhuang XQ, Wang F, Wang PF, Tao SL, Zhang XH, Wu SK, Lee ST (2007) Fluorescence turn on of coumarin derivatives by metal cations: a new signaling mechanism based on C=N isomerization. Org Lett 9(1):33–36.  https://doi.org/10.1021/ol062518z Google Scholar
  42. 42.
    Jiang GY, Zeng GJ, Zhu WP, Li YD, Dong XB, Zhang GX, Fan X, Wang J, Wu Y, Tang BZ (2017) A selective and light-up fluorescent probe for beta-galactosidase activity detection and imaging in living cells based on an AIE tetraphenylethylene derivative. Chem Commun 53(32):4505–4508.  https://doi.org/10.1039/c7cc00249a Google Scholar
  43. 43.
    Cui GL, Lan ZG, Thiel W (2012) Intramolecular hydrogen bonding plays a crucial role in the Photophysics and photochemistry of the GFP chromophore. J Am Chem Soc 134(3):1662–1672.  https://doi.org/10.1021/ja208496s Google Scholar
  44. 44.
    Xiao HD, Chen K, Cui DD, Jiang NN, Yin G, Wang J, Wang R (2014) Two novel aggregation-induced emission active coumarin-based Schiff bases and their applications in cell imaging. New J Chem 38(6):2386–2393.  https://doi.org/10.1039/c3nj01557b Google Scholar
  45. 45.
    Xu C, Li HD, Yin BZ (2015) A colorimetric and ratiometric fluorescent probe for selective detection and cellular imaging of glutathione. Biosens Bioelectron 72:275–281.  https://doi.org/10.1016/j.bios.2015.05.030 Google Scholar
  46. 46.
    Zhu BC, Zhang XL, Li YM, Wang PF, Zhang HY, Zhuang XQ (2010) A colorimetric and ratiometric fluorescent probe for thiols and its bioimaging applications. Chem Commun 46(31):5710–5712.  https://doi.org/10.1039/c0cc00477d Google Scholar

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© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  1. 1.College of Chemistry and BioengineeringGuilin University of TechnologyGuilinPeople’s Republic of China
  2. 2.Guangxi Key Laboratory of Electrochemical and Magnetochemical Functional MaterialsGuangxi Colleges and Universities Key Laboratory of Food Safety and DetectionGuilinPeople’s Republic of China

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