Advertisement

Russian Journal of Organic Chemistry

, Volume 55, Issue 6, pp 866–873 | Cite as

A Novel Fluorescent Probe Based on Spiro[chromeno[2,3-c]pyrazole-4,1′-[2]benzofuran]-3′-one for Detecting Copper(II) ions in Aqueous Solution

  • Yongshuang Yue
  • Zhengfeng XieEmail author
  • Yicheng Chu
  • Wei Shi
Review
  • 16 Downloads

Abstract

A novel fluorescent probe, DHMP {7-(dibutylamino)-3-methyl-1H,3′H-spiro[chromeno[2,3-c]pyrazole-4,1′-[2]benzofuran]-3′-one} was designed and synthesized by condensation of 2-[4-(dibutylamino)-2-hydroxybenzoyl]benzoic acid with 5-methyl-2,4-dihydropyrazol-3-one. The ultraviolet absorption and fluorescence emission spectra of DHMP showed a clear pH dependence and highly selective and sensitive response to copper(II) ions in aqueous medium. The detection limit of Cu2+ was estimated at 9.05 × 10−8 M.

Keywords

1,4-dihydrochromeno[2,3-c]pyrazole 7-(dibutylamino)-3-methyl- 1H,3′H-spiro[chromeno [2,3-c]-pyrazole-4,1′-[2]benzofuran]-3′-one fluorescent probe copper ion detection pH aqueous medium 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Zhu, D., Luo, Y., Shuai, L., Xie, W., Yan, X., Duan, Z., and Cai, W., Tetrahedron Lett., 2016, vol. 57, no. 48, p. 5326.CrossRefGoogle Scholar
  2. 2.
    Liu, S., Liu, Y., Pan, H., Chen, H. and Li, H., Tetrahedron Lett., 2018, vol. 59, no. 2, p. 108.CrossRefGoogle Scholar
  3. 3.
    Li, Y., Sun, M., Zhang, K., Zhang, Y., Yan, Y., Lei, K., Wu, L., Yu, H., and Wang, S., Sens. Actuators, B, 2017, vol. 243, p. 36.CrossRefGoogle Scholar
  4. 4.
    Cheng, D., Liu, X., Yang, H., Zhang, T., Han, A., and Zang, L., Sensors, 2017, vol. 17, no. 1, p. 35.Google Scholar
  5. 5.
    Barnham, K.J., Masters, C.L., and Bush, A.I., Nat. Rev. Drug Discovery, 2004, vol. 3, no. 3, p. 205.CrossRefPubMedGoogle Scholar
  6. 6.
    Bourassa, M.W. and Miller, L.M., Metallomics, 2012, vol. 4, no. 8, p. 721.CrossRefPubMedPubMedCentralGoogle Scholar
  7. 7.
    Peng, D., Hu, B., Kang, M., Wang, M., He, L., Zhang, Z., and Fang, S., Appl. Surf. Sci., 2016, vol. 390, p. 422.CrossRefGoogle Scholar
  8. 8.
    Xu, L., Wei, S., Diao, Q., Ma, P., Liu, X., Sun, Y., Song, D., and Wang, X., Sens. Actuators, B, 2017, vol. 246, p. 395.CrossRefGoogle Scholar
  9. 9.
    Ren, D., Liu, Y., Liu, X., Li, Z., Li, H., and Yang, X.F., Sens. Actuators, B, 2017, vol. 255, p. 2321.CrossRefGoogle Scholar
  10. 10.
    Gu, B., Huang, L., Su, W., Duan, X., Li, H., Yao, S., Anal. Chim. Acta, 2017, vol. 954, p. 97.CrossRefPubMedGoogle Scholar
  11. 11.
    Shen, Y., Zhang, X., Zhang, C., Zhang, Y., Jin, J., and Li, H., Spectrochim, Acta, Part A, 2017, vol. 191, p. 427.CrossRefGoogle Scholar
  12. 12.
    Hong, M., Lu, S., Lv, F., and Xu, D., Dyes Pigm., 2016, vol. 127, p. 94.CrossRefGoogle Scholar
  13. 13.
    Long, Y., Zhou, J., Yang, M.P., Liu, X.J., Zhang, M., and Yang, B.Q., Sens. Actuators, B, 2016, vol. 232, p. 327.CrossRefGoogle Scholar
  14. 14.
    Zhang, B., Diao, Q., Ma, P., Liu, X., Song, D., and Wang, X., Sens. Actuators, B, 2016, vol. 225, p. 579.CrossRefGoogle Scholar
  15. 15.
    Li, C.R., Yang, Z.Y., and Li, S.L., J. Lumin., 2018, vol. 198, p. 327.CrossRefGoogle Scholar
  16. 16.
    Yu, C., Wen, Y., and Zhang, J., Sensors, 2014, vol. 14, no. 11, p. 21375.CrossRefPubMedGoogle Scholar
  17. 17.
    Kaewtong, C., Pulpoka, B., and Tuntulani, T., Dyes Pigm., 2015, vol. 123, p. 204.CrossRefGoogle Scholar
  18. 18.
    Long, L., Wu, Y., Wang, L., Gong, A., Hu, R., and Zhang, C., Anal. Chim. Acta, 2016, vol. 908, p. 1.CrossRefPubMedGoogle Scholar
  19. 19.
    Li, Z., Geng, Z.-R., Zhang, C., Wang, X.-B., and Wang, Z.-L., Biosens. Bioelectron., 2015, vol. 72, p. 1.CrossRefPubMedGoogle Scholar
  20. 20.
    Xiong, X., Song, F., Wang, J., Zhang, Y., Xue, Y., Sun, L., Jiang, N., Gao, P., Tian, L., and Peng, X., J. Am. Chem. Soc., 2014, vol. 136, no. 27, p. 9590.CrossRefPubMedGoogle Scholar
  21. 21.
    Li, P., He, H., Wang, Z., Feng, M., Jin, H., Yun, W., Zhang, L., Zhang, L., and Tang, X., Anal. Chem., 2015, vol. 88, no. 1, p. 883.CrossRefPubMedGoogle Scholar
  22. 22.
    Lei, F., Shi, W., Ma, J., Chen, Y., Fan, K., Hui, Y., and Xie, Z., Sens. Actuators, B, 2016, vol. 237, p. 563.CrossRefGoogle Scholar
  23. 23.
    Lin, H., Shi, W., Tian, Y., Ma, F., Xu, L., Ma, J., Hui, Y., and Xie, Z., J. Lumin., 2015, vol. 157, p. 280.CrossRefGoogle Scholar
  24. 24.
    Shi, W., Chen, Y., Chen, X., Xie, Z., and Hui, Y., J. Lumin., 2016, vol. 174, p. 56.CrossRefGoogle Scholar
  25. 25.
    Ma, J., Shi, W., Feng, L., Chen, Y., Fan, K., Hao, Y., Hui, Y., and Xie, Z., RSC Adv., 2016, vol. 6, no. 33, p. 28034.CrossRefGoogle Scholar
  26. 26.
    Wang, X., Shi, W., Feng, L., Ma, J., Li, Y., Kong, X., Chen, Y., Hui, Y., and Xie, Z., Inorg. Chem. Commun., 2017, vol. 79, p. 50.CrossRefGoogle Scholar
  27. 27.
    Xie, Z., Kong, X., Feng, L., Ma, J., Li, Y., Wang, X., Bao, W., Shi, W., and Hui, Y., Sens. Actuators, B, 2018, vol. 257, p. 154.CrossRefGoogle Scholar
  28. 28.
    Hao, Y., Xie, Z., Bao, W., Wang, X., and Shi, W., Chin. J. Org. Chem., 2018, vol. 38, p. 2109.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • Yongshuang Yue
    • 1
  • Zhengfeng Xie
    • 1
    Email author
  • Yicheng Chu
    • 1
  • Wei Shi
    • 1
  1. 1.Oil & Gas Field Applied Chemistry Key Laboratory of Sichuan Province, College of Chemistry and Chemical EngineeringSouthwest Petroleum UniversityChengduChina

Personalised recommendations