Skip to main content
SpringerLink
Log in

Chiral amide-bonded hydroxyquinoline-substituted porphyrin fluorescent probes “off–on–off” pH sensing properties

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

Herein, a series of four amide-bonded hydroxyquinoline-substituted porphyrins have been prepared and characterized. Trends in the electronic structures are investigated by spectroscopic and electrochemical analysis to explore the effect of the functional amide-bonded hydroxyquinoline units. Also, the selective pH sensing properties were also performed and their plausible mechanism were also proposed. And the proposed mechanisms is the photoinduced electron transfer mechanism.

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

Similar content being viewed by others

References

  1. Albrecht, M., Witt, K., Wegelius, E.: Solid state structures of amide-substituted 8-hydroxyquinoline derivatives. Tetrahedron 56(4), 591–594 (2000)

    Article  CAS  Google Scholar 

  2. Han, J., Burgess, K.: Fluorescent indicators for intracellular pH. Chem. Rev. 110(5), 2709–2728 (2010)

    Article  CAS  PubMed  Google Scholar 

  3. Yan, Q., Wang, Y., Wang, Z.: A novel water-soluble flavonol-based fluorescent probe for highly specific and sensitive detection of Al3+ and its application in onion and zebrafish. Spectrochim Acta A 279, 121384 (2022)

    Article  CAS  Google Scholar 

  4. Song, Y., Tao, J.Y., Wang, Y.: A novel dual-responsive fluorescent probe for the detection of copper(II) and nickel(II) based on BODIPY derivatives. Inorg. Chim. Acta 516, 120099 (2021)

    Article  CAS  Google Scholar 

  5. Chen, Y., Xian, G., Yan, H., et al.: One-dimensional La(III) coordination polymer displaying multi-responsive luminescence activities towards Fe3+, acetone and benzothiozoles. Solid State Chem. 296, 121952 (2021)

    Article  CAS  Google Scholar 

  6. Yu, Y., Wang, Y., Xu, H.: Dual-responsive luminescent sensors based on two Cd-MOFs: rare enhancement toward acac and quenching toward Cr2O72−. CrystEngComm 22, 3759–3767 (2020)

    Article  CAS  Google Scholar 

  7. Karastogianni, S., Girousi, S., Sotiropoulos, S.: pH: principles and measurement. Encycl Food Health 4, 333–338 (2015)

    Google Scholar 

  8. Yin, J., Hu, Y., Yoon, J.: Fluorescent probes and bioimaging: alkali metals, alkaline earth metals and pH. Chem. Soc. Rev. 44(14), 4619–4644 (2015)

    Article  CAS  PubMed  Google Scholar 

  9. Bag, R., Sikdar, Y., Sahu, S.: A versatile quinoxaline derivative serves as a colorimetric sensor for strongly acidic pH. Dalton Trans. 47(47), 17077–17085 (2018)

    Article  CAS  PubMed  Google Scholar 

  10. Edinger, A.L., Thompson, C.B.: Death by design: apoptosis, necrosis and autophagy. Curr. Opin. Cell Biol. 16(6), 663–669 (2004)

    Article  CAS  PubMed  Google Scholar 

  11. Ning, Y., Wang, X., Sheng, K.: A novel colorimetric and fluorescence turn-on pH sensor with a notably large Stokes shift for its application. New J. Chem. 42(17), 14510–14516 (2018)

    Article  CAS  Google Scholar 

  12. Li, M., Yang, W., Qiu, P., et al.: Two efficient pH sensors based on heteronuclear metal-organic frameworks. Luminescence 205, 380–384 (2019)

    Article  CAS  Google Scholar 

  13. Bhuniya, S., Maiti, S., Kim, E.J.: An activatable theranostic for targeted cancer therapy and imaging. Angew. Chem. Int. Ed. 53(17), 4469–4474 (2014)

    Article  CAS  Google Scholar 

  14. Chu, B., Song, B., Ji, X.: Fluorescent silicon nanorods-based ratiometric sensors for long-term and real-time measurements of intracellular pH in live cells. Anal. Chem. 89(22), 12152–12159 (2017)

    Article  CAS  PubMed  Google Scholar 

  15. Xu, L., Yan, X., Yuan, C.: An unexpected dual-response pH probe based on acridine. RSC Adv. 8(61), 35289–35293 (2018)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Ge, Y., Wei, P., Wang, T.: A simple fluorescent probe for monitoring pH in cellsbased on new fluorophorepyrido [1,2-a] benzimidazole. Sens. Actuators B 254, 314–320 (2018)

    Article  CAS  Google Scholar 

  17. Si, H.Y., Cho, M.K., Kang, J.S.: Carboxylate-containing two-photon probe for the simultaneous detection of extra- and intracellular pH values in colon cancer tissue. Anal. Chem. 90(13), 8058–8064 (2018)

    Article  CAS  PubMed  Google Scholar 

  18. Dong, B., Song, X., Kong, X.: A tumor-targeting and lysosome-specific two-photon fluorescent probe for imaging pH changes in living cells. J. Mater. Chem. B 5(5), 988–995 (2017)

    Article  CAS  PubMed  Google Scholar 

  19. Wang, F., Liu, D., Shen, Y.: Chiral modulation from molecular to macroscopic levels by synthetic chiral-amide-bonded porphyrin dimers. Dyes Pigm. 166, 92–97 (2019)

    Article  CAS  Google Scholar 

  20. Vegesna, G.K., Janjanam, J., Bi, J.: pH-activatable near-infrared fluorescent probes for detection of lysosomal pH inside living cells. J. Mater. Chem. B 2(28), 4500–4508 (2014)

    Article  CAS  PubMed  Google Scholar 

  21. Kim, N.H., Won, M., Kim, J.S.: A highly sensitive and fast responsive fluorescent probe for detection of Gold(III) ions based on the AIEgen disaggregation. Dyes Pigm. 160, 647–653 (2019)

    Article  CAS  Google Scholar 

  22. Yin, H.S., Li, B.C., Zhou, Y.L.: Signal-on fluorescence biosensor for microRNA-21 detection based on DNA strand displacement reaction and Mg2+-dependent DNAzyme cleavage. Biosens. Bioelectron. 96, 106–112 (2017)

    Article  CAS  PubMed  Google Scholar 

  23. Zhou, H., Tang, J., Sun, L.: H2S2-triggered off-on fluorescent indicator with endoplasmic reticulum targeting for imaging in cells and zebrafishes. Sens. Actuators B 278, 64–72 (2019)

    Article  CAS  Google Scholar 

  24. Tian, X., Li, Z., Pang, Y., et al.: Benzoyl peroxide detection in real samples and zebrafish imaging by a designed near-infrared fluorescent probe. J. Agric. Food Chem. 65(43), 9553–9558 (2017)

    Article  CAS  PubMed  Google Scholar 

  25. Albert, A., Phillips, J.N.: Ionization constants of heterocyclic substances. Part II. Hydroxy-derivatives of nitrogenous six-membered ring-compounds. J. Chem. Soc. (1956). https://doi.org/10.1039/jr9560001294

    Article  Google Scholar 

  26. Bardez, E., Devol, I., Larrey, B.: Excited-state processes in 8-hydroxyquinoline: photoinduced tautomerization and solvation effects. J. Phys. Chem. B 101(39), 7786–7793 (1997)

    Article  CAS  Google Scholar 

  27. Xu, L., Qin, M.F., Zhang, X.M.: Chiral modulation from molecular to macroscopic levels by synthetic chiral-amide-bonded porphyrin dimers. Dyes Pigm. 171, 107637 (2019)

    Article  Google Scholar 

  28. Zhu, W.H., Hadier, S., Zhang, H.L.: Synthesis and properties of chiral amide-bonded porphyrin dimers with various functional bridging blocks. Dyes Pigm. 171, 107740 (2019)

    Article  CAS  Google Scholar 

  29. Zhu, W.H., Zhang, H.L., Liu, S.Q.: Efficient nonlinear-optical behaviors of chiral-amide-bonded porphyrin noncovalent functionalized MWCNTs by terminated pyrene units. New J. Chem. 44, 14890 (2020)

    Article  CAS  Google Scholar 

  30. Zhang, L., Meggers, E.: A simple glycol nucleic acid. J. Am. Chem. Soc. 127(1), 74–75 (2005)

    Article  CAS  PubMed  Google Scholar 

  31. Moon, S.Y., Cha, N.R., Kim, Y.H.: New Hg2+-selective chromo- and fluoroionophore based upon 8-hydroxyquinoline. J. Org. Chem. 69(1), 181–183 (2004)

    Article  CAS  PubMed  Google Scholar 

  32. Chen, C.H., Shi, J.: Metal chelates as emitting materials for organic electroluminescence. Coord. Chem. Rev. 171(1), 161–174 (1998)

    Article  CAS  Google Scholar 

  33. Liang, X., Qin, M.F., Zhou, L., Liu, T.T., Li, M.Z., Mack, J., Ndebeleb, N., Nyokong, T., Zhu, W.H.: Porphyrin dimers with a bridging chiral amide-bonded benzo-moiety: influence of positional isomerism on the molecular chirality. Dyes Pigm. 154, 229–233 (2018)

    Article  CAS  Google Scholar 

  34. Liang, X., Qin, M.F., Zhang, X.M., Mack, J., Soy, R.C., Nyokong, T., Zhu, W.H.: Chiral modulation from molecular to macroscopic levels by synthetic chiral-amide-bonded porphyrin dimers. Dyes Pigm. 171, 107637 (2019)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the National Natural Science Foundation of China (21701058), the China post-doc foundation (No. 2018M642183), the Lanzhou High Talent Innovation and Entrepreneurship Project (No. 2018-RC-105) and the Jiangsu University.

Author information

Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, People’s Republic of China

    Syed Najeeb-Uz-Zaman Haider, Tingting Gu, Weihua Zhu & Xu Liang

  2. Lanzhou Petrochemical University of Vocational Technology, Lanzhou, 730050, P. R. China

    Rongping Tang & Xu Liang

Authors
  1. Syed Najeeb-Uz-Zaman Haider
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tingting Gu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Rongping Tang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Weihua Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Xu Liang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Rongping Tang, Weihua Zhu or Xu Liang.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 2568 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Haider, S.NUZ., Gu, T., Tang, R. et al. Chiral amide-bonded hydroxyquinoline-substituted porphyrin fluorescent probes “off–on–off” pH sensing properties. J Incl Phenom Macrocycl Chem 102, 881–892 (2022). https://doi.org/10.1007/s10847-022-01168-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-022-01168-9

Keywords

Search

Navigation