Skip to main content
SpringerLink
Log in

A Novel “Turn-on” Triphenylamine-Based Fluorescent Probe for Ultrasensitive Detection of Al3+ and Its Application on Test Strips

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

A triphenylamine-based “turn-on” fluorescent chemosensor, (E)-3-(benzyloxy)-N′-{[4′-(diphenyl­amino)-4-hydroxy[1,1′-biphenyl]-3-yl]methylidene}benzohydrazide (BDHBMB), containing a 3-benzyloxy­benzo­hydrazide moiety was successfully synthesized. It showed high selectivity, excellent anti-interference performance, and remarkable sensitivity for Al3+ ions in methanol solution. After the addition of Al3+, BDHBMB exhibited strong fluorescence emission (18 times enhancement) at λ 573 nm due to the formation of a rigid conjugate structure based on chelation-enhanced fluorescence (CHEF) mechanism. A great linearity with a correlation coefficient R2 of 0.99 was observed in the concentration range 0–60 μM. The binding constant and the limit of detection (LOD) for Al3+ were calculated to be 1.48×103 M–1 and 8.94×10–8 M, respectively. The “turn-on” fluorescent probe was successfully applied to visual detection of Al3+ in test paper.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme
Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.
Fig. 6.
Fig. 7.
Fig. 8.

Similar content being viewed by others

REFERENCES

  1. Neupane, L.N., Mehta, P.K., Oh, S., Park, S.H., and Lee, K.H., Analyst, 2018, vol. 143, p. 5285. https://doi.org/10.1039/c8an01221k

    Article  CAS  Google Scholar 

  2. Sudheer, Kumar, V., Kumar, P., and Gupta, R., New J. Chem., 2020, vol. 44, p. 13285. https://doi.org/10.1039/d0nj00517g

    Article  CAS  Google Scholar 

  3. Das, B., Dey, S., Maiti, G.P., Bhattacharjee, A., Dhara, A., and Jana, A., New J. Chem., 2018, vol. 42, p. 9424. https://doi.org/10.1039/c7pp00286f

    Article  CAS  Google Scholar 

  4. Pan, W.H., Zheng, C.H., Liao, G.M., Liu, G., and Pu, S.Z., Microchem. J., 2021, vol. 163, article ID 105887. https://doi.org/10.1016/j.microc.2020.105887

  5. Chandra, R., Manna, A.K., Rout, K., Mondal, J., and Patra, G.K., RSC Adv., 2018, vol. 8, p. 35946. https://doi.org/10.1039/c8ra07041e

    Article  CAS  Google Scholar 

  6. Naskar, B., Das, K., Mondal, R.R., Maiti, D.K., Requena, A., Cerón-Carrasco, J.P., Prodhan, C., Chaudhuri, K., and Goswami, S., New J. Chem., 2018, vol. 42, p. 2933. https://doi.org/10.1039/c7nj03955g

    Article  CAS  Google Scholar 

  7. Hiremath, S.D., Gawas, R.U., Mascarenhas, S.C., Ganguly, A., Banerjee, M., and Chatterjee, A., New J. Chem., 2019, vol. 43, p. 5219. https://doi.org/10.1039/c9nj00418a

    Article  CAS  Google Scholar 

  8. Roy, A., Mukherjee, R., Dam, B., Dam, S., and Roy, P., New J. Chem., 2018, vol. 42, p. 8415. https://doi.org/10.1039/c8nj01130c

    Article  CAS  Google Scholar 

  9. Rangasamy, M. and Palaninathan, K., New J. Chem., 2018, vol. 42, p. 10891. https://doi.org/10.1039/c8nj01211c

    Article  CAS  Google Scholar 

  10. Bai, L.P., Xu, Y.H., Li, L.X., Tao, F.R., Wang, S.S., Wang, L.P., and Li, G., New J. Chem., 2020, vol. 44, p. 11148. https://doi.org/10.1039/d0nj01856b

    Article  CAS  Google Scholar 

  11. Yan, C.R., Guo, L.L., Shao, X., Shu, Q., Guan, P., Wang, J.W., Hu, X.L., and Wang, C.L., Anal. Bioanal. Chem., 2021, vol. 413, p. 3965. https://doi.org/10.1007/s00216-021-03348-x

    Article  CAS  Google Scholar 

  12. Aydin, D., Gunay, I.B., Karuk Elmas, S.N., Savran, T., Arslan, F.N., Sadi, G., and Yilmaz, I., New J. Chem., 2020, vol. 44, p. 12079. https://doi.org/10.1039/d0nj02487b

    Article  CAS  Google Scholar 

  13. Sun, X.J., Liu, T.T., Fu, H., Li, N.N., Xing, Z.Y., and Yang, F., Front. Chem., 2019, vol. 7, p. 549. https://doi.org/10.3389/fchem.2019.00549

    Article  CAS  Google Scholar 

  14. Liu, T.Q., Wan, X.J., and Yao, Y.W., Sens. Actuators, B, 2018, vol. 254, p. 1094. https://doi.org/10.1016/j.snb.2017.07.114

    Article  CAS  Google Scholar 

  15. Hossain, S.M., Singh, K., Lakma, A., Pradhan, R.N., and Singh, A.K., Sens. Actuators, B, 2017, vol. 239, p. 1109. https://doi.org/10.1016/j.snb.2016.08.093

    Article  CAS  Google Scholar 

  16. Pramanik, S., Manna, S.K., Pathak, S., Mondal, D., Pal, K., and Mukhopadhyay, S., New J. Chem., 2020, vol. 44, p. 13259. https://doi.org/10.1039/d0nj02117b

    Article  CAS  Google Scholar 

  17. Liu, F.F., Fan, C.B., Tu, Y.Y., and Pu, S.Z., RSC Adv., 2018, vol. 8, p. 31113. https://doi.org/10.1039/c8ra05439h

    Article  CAS  Google Scholar 

  18. Song, H.M., Liu, G., Fan, C.B., and Pu, S.Z., J. Rare Earths, 2020, vol. 39, p. 460. https://doi.org/10.1016/j.jre.2020.02.020

    Article  CAS  Google Scholar 

  19. De Benedetto, G.E., Di Masi, S., Pennetta, A., and Malitesta, C., Biosensors, 2019, vol. 9, article no. 26. https://doi.org/10.3390/bios9010026

  20. Nobuhiko, I., Hitoshi, H., and Takao, Y., Anal. Chem., 2000, vol. 72, p. 4812. https://doi.org/10.1021/ac000312k

    Article  CAS  Google Scholar 

  21. Chen, Z.-L. and Naidu, R., J. Chromatogr. A, 2002, vol. 996, p. 245. https://doi.org/10.1016/s0021-9673(02)00741-0

    Article  Google Scholar 

  22. Saito, S., Tamura, J., Sato, M., and Aoyama, M., J. Chromatogr. A, 2008, vol. 1190, p. 198. https://doi.org/10.1016/j.chroma.2008.03.018

    Article  CAS  Google Scholar 

  23. Shingo, S., Tetsuya, A., Suwaru, H., and Kunihiko, A., Anal. Chem., 2005, vol. 77, p. 5332. https://doi.org/10.1021/ac050380c

    Article  CAS  Google Scholar 

  24. Diao, Q.P., Ma, P.Y., Lv, L.L., Li, T.C., Sun, Y., Wang, X.H., and Song, D.Q., Sens. Actuators, B, 2016, vol. 229, p. 138. https://doi.org/10.1016/j.snb.2016.01.136

    Article  CAS  Google Scholar 

  25. Wang, B.G., Liu, X., Duan, W.M., Dai, S.S., and Lu, H.S., Microchem. J., 2020, vol. 156, article ID 104807. https://doi.org/10.1016/j.microc.2020.104807

  26. Wang, P., Liu, L., Meng, F., Khan, M.A., and Li, H., Front. Chem., 2020, vol. 8, article ID 607614. https://doi.org/10.3389/fchem.2020.607614

  27. Zhong, W.X., Wang, L.Z., Fang, S.M., Qin, D.W., Zhou, J.H., Yang, G., and Duan, H.D., RSC Adv., 2020, vol. 10, p. 3048. https://doi.org/10.1039/c9ra08428b

    Article  CAS  Google Scholar 

  28. Kim, H., Suh, B., and Kim, C., J. Chin. Chem. Soc., 2022, vol. 69, p. 366. https://doi.org/10.1002/jccs.202100374

    Article  CAS  Google Scholar 

  29. Li, N.N., Zeng, S., Li, M.Q., Ma, Y.Q., Sun, X.J., Xing, Z.Y., and Li, J.L., J. Fluoresc., 2018, vol. 28, p. 347. https://doi.org/10.1007/s10895-017-2197-9

    Article  CAS  Google Scholar 

  30. Cao, Y.L., Xi, W.G., Wang, L.K., Wang, H.Z., Kong, L., Zhou, H.P., Wu, J.Y., and Tian, Y.P., RSC Adv., 2014, vol. 4, p. 24649. https://doi.org/10.1039/C4RA03042G

    Article  CAS  Google Scholar 

  31. Goudappagouda, Asokan, K., Nayak, R., Krishnan, R., and Babu, S.S., Dyes Pigm., 2020, vol. 173, article ID 107931. https://doi.org/10.1016/j.dyepig.2019.107931

  32. Tu, J., Fan, Y.H., Wang, J.Q., Li, X.Y., Liu, F., Han, M.M., Wang, C., Li, Q.Q., and Li, Z., J. Mater. Chem. C, 2019, vol. 7, p. 12256. https://doi.org/10.1039/C9TC03515J

    Article  CAS  Google Scholar 

  33. Qin, J.C., Fan, L., Wang, B.D., Yang, Z.Y., and Li, T.R., Anal. Methods, 2015, vol. 7, p. 716. https://doi.org/10.1039/c4ay02351j

    Article  CAS  Google Scholar 

  34. Kumar, M., Kumar, A., Kishor, S., Kumar, S., Kumar, A., Manav, N., Bhagi, A.K., Kumar, S., and John, R.P., J. Mol. Struct., 2022, vol. 1247, article ID 131257. https://doi.org/10.1016/j.molstruc.2021.131257

  35. Mu, Y.L., Zhang, C.J., Gao, Z.J., Zhang, X., Lu, Q., Yao, J.S., and Xing, S., Synth. Met., 2020, vol. 262, article ID 116334. https://doi.org/10.1016/j.synthmet.2020.116334

  36. Qin, J.C., Cheng, X.Y., Yu, K.C., Fang, R., Wang, M.F., and Yang, Z.Y., Anal. Methods, 2015, vol. 7, no. 16, p. 6799. https://doi.org/10.1039/c5ay01160d

    Article  CAS  Google Scholar 

  37. Yan, L.Q., Ma, Y., Cui, M.F., and Qi, Z.J., Anal. Methods, 2015, vol. 7, p. 6133. https://doi.org/10.1039/c5ay01466b

    Article  CAS  Google Scholar 

  38. Li, Z., Wang, Q., Wang, J., Jing, X.M., Wang, S.J., Xiao, L.W., and Li, L.L., Inorg. Chim. Acta, 2020, vol. 500, article ID 119231. https://doi.org/10.1016/j.ica.2019.119231

  39. Yin, P.C., Niu, Q.F., Wei, T., Li, T.D., Li, Y., and Yang, Q.X., J. Photochem. Photobiol., A, 2020, vol. 389, article ID 112249. https://doi.org/10.1016/j.jphotochem.2019.112249

  40. Zhu, G.H., Huang, Y., Wang, C., Lu, L.X., Sun, T.M., Wang, M., Tang, Y.F., Shan, D.D., Wen, S.J., and Zhu, J.L., Spectrochim. Acta, Part A, 2019, vol. 210, p. 105. https://doi.org/10.1016/j.saa.2018.11.006

    Article  CAS  Google Scholar 

  41. Tian, H., Qiao, X., Zhang, Z.L., Xie, C.Z., Li, Q.Z., and Xu, J.Y., Spectrochim. Acta, Part A, 2019, vol. 207, p. 31. https://doi.org/10.1016/j.saa.2018.08.063

    Article  CAS  Google Scholar 

  42. Erdemir, S., Malkondu, S., and Kararkurt, S., Analyst, 2020, vol. 145, p. 3725. https://doi.org/10.1039/c9an02500f

    Article  CAS  Google Scholar 

Download references

Funding

This study was financially supported by the National Natural Science Foundation of China (21861017, 41867053), the key project of Natural Science Foundation of Jiangxi Province (20192ACBL20011), and the Key Project of the Science Funds of Jiangxi Education Office (GJJ201105).

Author information

Authors and Affiliations

  1. Jiangxi Key Laboratory of Organic Chemistry, College of Chemistry and Chemical Engineering, Jiangxi Science and Technology Normal University, 330031, Nanchang, China

    L. Xie, X. Wang, R. H. Yao, T. T. Fan, X. X. Chen, C. B. Fan & S. Z. Pu

  2. Department of Ecology and Environment, Yuzhang Normal University, 330103, Nanchang, China

    S. Z. Pu

Authors
  1. L. Xie
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. X. Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. H. Yao
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. T. T. Fan
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. X. X. Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. C. B. Fan
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. S. Z. Pu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to C. B. Fan or S. Z. Pu.

Ethics declarations

The authors declare the absence of conflict of interest.

Supplementary information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Xie, L., Wang, X., Yao, R.H. et al. A Novel “Turn-on” Triphenylamine-Based Fluorescent Probe for Ultrasensitive Detection of Al3+ and Its Application on Test Strips. Russ J Org Chem 58, 1821–1830 (2022). https://doi.org/10.1134/S1070428022120119

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428022120119

Keywords:

Search

Navigation