Issue

Vol. 35 No. 7 (2023): Vol 35 Issue 7 (2023)

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

A Rhodamine Based Fluorometric and Colorimetric Probe for Detection of pH in Aqueous Medium

https://doi.org/10.14233/ajchem.2023.27951
Subhodip Samanta
Department of Chemistry, Maulana Azad College, Kolkata-700013, India
https://orcid.org/0000-0003-1455-8980

Corresponding Author(s) : Subhodip Samanta

subhodip.samanta@gmail.com

Asian Journal of Chemistry, Vol. 35 No. 7 (2023): Vol 35 Issue 7 (2023)

Abstract

Present study involves a rhodamine based fluorescent probe, which is reported to exhibit high fluorescence and colorimetric response in the pH range 2.0-5.5, where 55-fold fluorescence intensity change was identified with the lowering of pH of the medium. The working principle of the probe is based on its reversible structural inter-conversion between spirocyclic ring-close (non-fluorescent) and spirocyclic ringopen (fluorescent) forms of rhodamine base along with a reversible color change between colourless and pink with change in the pH medium. The closed spirocyclic form (AX) of the probe converts gradually into the spirocyclic open-ring (HAX) with increasing acidity of the medium and which in turn results in the strong orange fluorescence emission along with visible colorimetric responses. The calculated pKa ~ 4.0 for such conversion indicates that the probe can be useful to detect the pH of the aqueous medium in the range 3.0-5.0. The probe displays high sensitivity, good photostability, and reversible pH dependence. Detailed analysis of the pH sensing capability of the probe were performed by means of UV-vis spectroscopy, steady state and time resolved fluorescence techniques and DFT/TD-DFT based theoretical calculations.

Keywords

Rhodamine Fluorescence Colorimetry pH Extreme acidity
Samanta, S. (2023). A Rhodamine Based Fluorometric and Colorimetric Probe for Detection of pH in Aqueous Medium. Asian Journal of Chemistry, 35(7), 1665–1671. https://doi.org/10.14233/ajchem.2023.27951
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX
References
  1. C. Das Neves Gomes, O. Jacquet, C. Villiers, P. Thuéry, M. Ephritikhine and T. Cantat, Angew. Chem. Int. Ed., 51, 1. (2012); https://doi.org/10.1002/anie.201106864
  2. Y. Tan, J. Yu, J. Gao, Y. Cui, Z. Wang, Y. Yang and G. Qian, RSC Adv., 3, 4872 (2013); https://doi.org/10.1039/c3ra00120b
  3. A. Kurkdjian and J. Guern, Annu. Rev. Plant Physiol. Plant Mol. Biol., 40, 271 (1989); https://doi.org/10.1146/annurev.pp.40.060189.001415
  4. J. Han and K. Burgess, Chem. Rev., 110, 2709 (2010); https://doi.org/10.1021/cr900249z
  5. A. Steinegger, O.S. Wolfbeis and S.M. Borisov, Chem. Rev., 120, 12357 (2020); https://doi.org/10.1021/acs.chemrev.0c00451
  6. L.D. Lavis, Biochemistry, 60, 3539 (2021); https://doi.org/10.1021/acs.biochem.1c00299
  7. D. Wencel, T. Abel and C. McDonagh, Anal. Chem., 86, 15 (2014); https://doi.org/10.1021/ac4035168
  8. L. Wu, X. Li, C. Huang and N. Jia, Anal. Chem., 88, 8332 (2016); https://doi.org/10.1021/acs.analchem.6b02398
  9. X. Li, X. Gao, W. Shi and H. Ma, Chem. Rev., 114, 590 (2014); https://doi.org/10.1021/cr300508p
  10. A.P. de Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, A.J.M. Huxley, C.P. McCoy, J.T. Rademacher and T.E. Rice, Chem. Rev., 97, 1515 (1997); https://doi.org/10.1021/cr960386p
  11. C. McDonagh, C.S. Burke and B.D. MacCraith, Chem. Rev., 108, 400 (2008); https://doi.org/10.1021/cr068102g
  12. J. Krämer, R. Kang, L.M. Grimm, L. De Cola, P. Picchetti and F. Biedermann, Chem. Rev., 122, 3459 (2022); https://doi.org/10.1021/acs.chemrev.1c00746
  13. X. Zhang, Y. Jiao, X. Jing, H. Wu, G. He and C. Duan, Dalton Trans., 40, 2522 (2011); https://doi.org/10.1039/c0dt01325k
  14. B. Tang, X. Liu, K. Xu, H. Huang, G. Yang and L. An, Chem. Commun., 3726, 3726 (2007); https://doi.org/10.1039/b707173f
  15. Z.-Q. Hu, M. Li, M.-D. Liu, W.-M. Zhuang and G.-K. Li, Dyes Pigments, 96, 71 (2013); https://doi.org/10.1016/j.dyepig.2012.07.012
  16. H.N. Kim, M.H. Lee, H.J. Kim, J.S. Kim and J. Yoon, Chem. Soc. Rev., 37, 1465 (2008); https://doi.org/10.1039/b802497a
  17. P. Ghosh and P. Roy, Chem. Commun., 59, 5174 (2023); https://doi.org/10.1039/D3CC00651D
  18. M. Tian, X. Peng, J. Fan, J. Wang and S. Sun, Dyes Pigments, 95, 112 (2012); https://doi.org/10.1016/j.dyepig.2012.03.008
  19. J.-L. Tan, T.-T. Yang, Y. Liu, X. Zhang, S.-J. Cheng, H. Zuo and H. He, Luminescence, 31, 865 (2016); https://doi.org/10.1002/bio.3043
  20. U.C. Saha, K. Dhara, B. Chattopadhyay, S.K. Mandal, S. Mondal, S. Sen, M. Mukherjee, S. van Smaalen and P. Chattopadhyay, Org. Lett., 13, 4510 (2011); https://doi.org/10.1021/ol201652r
  21. R. Gui, X. An and W. Huang, Anal. Chim. Acta, 767, 134 (2013); https://doi.org/10.1016/j.aca.2013.01.006
  22. B.K. McMahon, R. Pal and D.A. Parker, Chem. Commun., 49, 5363 (2013); https://doi.org/10.1039/c3cc42308e
  23. H.S. Lv, S.Y. Huang, B.X. Zhao and J.Y. Miao, Anal. Chim. Acta, 788, 177 (2013); https://doi.org/10.1016/j.aca.2013.06.038
  24. X.X. Zhao, X.P. Chen, S.L. Shen, D.P. Li, S. Zhou, Z.Q. Zhou, Y.H. Xiao, G. Xi, J.-Y. Miao and B.X. Zhao, RSC Adv., 4, 50318 (2014); https://doi.org/10.1039/C4RA07555B
  25. X.-F. Zhang, T. Zhang, S.-L. Shen, J.-Y. Miao and B.-X. Zhao, J. Mater. Chem. B Mater. Biol. Med., 3, 3260 (2015); https://doi.org/10.1039/C4TB02082K
  26. S.-L. Shen, X.-F. Zhang, S.-Y. Bai, J.-Y. Miao and B.X. Zhao, RSC Adv., 5, 13341 (2015); https://doi.org/10.1039/C4RA16398B
  27. W. Luo, H. Jiang, X. Tang and W. Liu, J. Mater. Chem. B Mater. Biol. Med., 5, 4768 (2017); https://doi.org/10.1039/C7TB00838D
  28. W. Zhang, B. Tang, X. Liu, Y. Liu, K. Xu, J. Ma, L. Tong and G. Yang, Analyst, 134, 367 (2009); https://doi.org/10.1039/B807581F
  29. S. Kang, S. Kim, Y.-K. Yang, S. Bae and J. Tae, Tetrahedron Lett., 50, 2010 (2009); https://doi.org/10.1016/j.tetlet.2009.02.087
  30. C. Wurth, M. Grabolle, J. Pauli, M. Spieles and U. Resch-Genger, Anal. Chem., 83, 3431 (2011); https://doi.org/10.1021/ac2000303
  31. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, G.A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. Marenich, J. Bloino, B.G. Janesko, R. Gomperts, B. Mennucci, H.P. Hratchian, J.V. Ortiz, A.F. Izmaylov, J.L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V.G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, J.M. Millam, M. Klene, C. Adamo, R. Cammi, J.W. Ochterski, R.L. Martin, K. Morokuma, O. Farkas, J.B. Foresman and D.J. Fox, Gaussian 09, Revision A.02, Gaussian, Inc., Wallingford CT (2016).
  32. Q.A. Best, R. Xu, M.E. McCarroll, L. Wang and D.J. Dyer, Org. Lett., 12, 3219 (2010); https://doi.org/10.1021/ol1011967
  33. Y. Mi, Z. Cao, Y. Chen, S. Long, Q. Xie, D. Liang, W. Zhu and J. Xiang, Sens. Actuators B Chem., 192, 164 (2014); https://doi.org/10.1016/j.snb.2013.10.103
  34. M. Dong, T.H. Ma, A.J. Zhang, Y.M. Dong, Y.W. Wang and Y. Peng, Dyes Pigments, 87, 164 (2010); https://doi.org/10.1016/j.dyepig.2010.03.015
  35. P. Mahato, S. Saha, E. Suresh, R. Di Liddo, P.P. Parnigotto, M.T. Conconi, M.K. Kesharwani, B. Ganguly and A. Das, Inorg. Chem., 51, 1769 (2012); https://doi.org/10.1021/ic202073q
  36. H. Zheng, Z.H. Qian, L. Xu, F.F. Yuan, L.D. Lan and J.G. Xu, Org. Lett., 8, 859 (2006); https://doi.org/10.1021/ol0529086
Read More
Author biographies is not available.
Download
AJC-35-7-16
Statistic
Read Counter : 1 Download : 1