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Electron-donating methoxy group enhances the stability and efficiency of indole-based fluorescent probe for detecting Cu2+

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Abstract

Two novel Schiff-base fluorescent probes bearing different substituents were synthesized by the reaction of indole derivatives with 4-aminoantipyrine. The fluorescent behavior toward Cu2+ was studied by analyzing ultraviolet–visible (UV–Vis) absorption spectra and fluorescence spectroscopy results, which demonstrated that compound 2 containing a methoxy moiety exhibited improved selectivity and stronger fluorescent emission for Cu2+. However, both of the evaluated probes were sensitive to Cu2+ at nM concentrations. Notably, compound 2 displayed remarkable fluorescence properties in a wide range of pH due to a stable chemical structure. The experimental data based on cyclic voltammetry (CV) were in good agreement with the fluorescence spectroscopy analysis and confirmed the formation of a fluorescent complex. In addition, the optimized geometry and related properties were established at B3LYP/6-31G using density functional theory (DFT) calculations. Compound 2, which was efficiently synthesized in the present study, demonstrates potential for Cu2+ detection in various analysis and testing fields.

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References

  1. Y.K. Jang, U.C. Nam, H.L. Kwon, I.H. Hwang, C. Kim, Dyes Pigments 99, 6 (2013)

    CAS  Google Scholar 

  2. Z. Yang, M. She, J. Zhang, X. Chen, Y. Huang, H. Zhu, P. Liu, J. Li, Z. Shi, Sensor. Actuat. B-Chem. 176, 482 (2013)

    CAS  Google Scholar 

  3. J.-C. Qin, Z.-Y. Yang, J. Photochem. Photobiol. A. 324, 152 (2016)

    CAS  Google Scholar 

  4. H. Zhou, J. Wang, Y. Chen, W. Xi, Z. Zheng, D. Xu, Y. Cao, G. Liu, W. Zhu, J. Wu, Y. Tian, Dyes Pigments 98, 1 (2013)

    CAS  Google Scholar 

  5. H. Shi, Y. Cui, Y. Gong, S. Feng, Spectrochim. Acta A. 161, 150 (2016)

    CAS  Google Scholar 

  6. Y.-W. Duan, H.-Y. Tang, Y. Guo, Z.-K. Song, M.-J. Peng, Y. Yan, Chin. Chem. Lett. 25, 1082 (2014)

    CAS  Google Scholar 

  7. J.C. Lee, H.B. Gray, J.R. Winkler, J. Am. Chem. Soc. 130, 6898 (2008)

    PubMed  PubMed Central  Google Scholar 

  8. N. Shao, J.Y. Jin, H. Wang, Y. Zhang, R.H. Yang, W.H. Chan, Anal. Chem. 80, 3466 (2008)

    CAS  PubMed  Google Scholar 

  9. L. Yang, W. Zhu, M. Fang, Q. Zhang, C. Li, Spectrochim. Acta A. 109, 186 (2013)

    CAS  Google Scholar 

  10. H.-G. Li, Z.-Y. Yang, D.-D. Qin, Inorg. Chem. Commun. 12, 494 (2009)

    CAS  Google Scholar 

  11. N.K. Hien, M.V. Bay, N.C. Bao, Q.V. Vo, N.D. Cuong, T.V. Thien, N.T.A. Nhung, D.U. Van, P.C. Nam, D.T. Quang, ACS Omega 5, 21241 (2020)

    CAS  PubMed  PubMed Central  Google Scholar 

  12. J.S. Becker, A. Matusch, C. Depboylu, J. Dobrowolska, M.V. Zoriy, Anal. Chem. 79, 6074 (2007)

    CAS  PubMed  Google Scholar 

  13. J. Buffle, M.L. Tercier-Waeber, TrAC, Trends Anal. Chem. 24, 172 (2005)

    CAS  Google Scholar 

  14. T.-W. Lin, S.-D. Huang, Anal. Chem. 73, 4319 (2001)

    CAS  PubMed  Google Scholar 

  15. G. Doner, A. Ege, Anal. Chim. Acta 547, 14 (2005)

    CAS  Google Scholar 

  16. G. Aragay, J. Pons, A. Merkoçi, Chem. Rev. 111, 3433 (2011)

    CAS  PubMed  Google Scholar 

  17. Y. Chen, X. Min, X. Zhang, F. Zhang, S. Lu, L.-P. Xu, X. Lou, F. Xia, X. Zhang, S. Wang, Biosens. Bioelectron. 111, 124 (2018)

    CAS  PubMed  Google Scholar 

  18. S. Suganya, S. Velmathi, D. MubarakAli, Dyes Pigments 104, 116 (2014)

    CAS  Google Scholar 

  19. L. Zhou, P. Cai, Y. Feng, J. Cheng, H. Xiang, J. Liu, D. Wu, X. Zhou, Anal. Chim. Acta. 735, 96 (2012)

    CAS  PubMed  Google Scholar 

  20. L. Ma, G. Liu, S. Pu, H. Ding, G. Li, Tetrahedron 72, 985 (2016)

    CAS  Google Scholar 

  21. L. Wang, J. Zhang, X. An, H. Duan, Org. Biomol. Chem. 18, 1522 (2020)

    CAS  PubMed  Google Scholar 

  22. Y. Huo, J. Miao, J. Fang, H. Shi, J. Wang, W. Guo, Chem. Sci. 10, 145 (2019)

    CAS  PubMed  Google Scholar 

  23. S. Singha, Y.W. Jun, S. Sarkar, K.H. Ahn, Acc. Chem. Res. 52, 2571 (2019)

    CAS  PubMed  Google Scholar 

  24. M. Zhou, X. Wang, K. Huang, Y. Huang, S. Hu, W. Zeng, Tetrahedron Lett. 58, 991 (2017)

    CAS  Google Scholar 

  25. M. Wei, Y. Zhang, H. Li, S. Yao, Anal. Methods 9, 3956 (2017)

    CAS  Google Scholar 

  26. Z. Xu, L. Zhang, R. Guo, T. Xiang, C. Wu, Z. Zheng, F. Yang, Sensor. Actuat. B-Chem. 156, 546 (2011)

    CAS  Google Scholar 

  27. L. Fan, T.-R. Li, B.-D. Wang, Z.-Y. Yang, C.-J. Liu, Spectrochim. Acta A. 118, 760 (2014)

    CAS  Google Scholar 

  28. C. Li, K. Xiang, Y. Liu, Y. Zheng, L. Pan, B. Tian, J. Zhang, Res. Chem. Intermed. 41, 5915 (2015)

    CAS  Google Scholar 

  29. S. Santhi, S. Amala, R. Renganathan, M. Subhashini, S.M. Basheer, Res. Chem. Intermed. 45, 4813 (2019)

    CAS  Google Scholar 

  30. C.-K. Lin, J.-S. Yang, Res. Chem. Intermed. 39, 19 (2013)

    CAS  Google Scholar 

  31. Y. Li, Y.-X. Ji, L.-J. Song, Y. Zhang, Z.-C. Li, L. Yang, W.-C. Huang, Res. Chem. Intermed. 44, 5169 (2018)

    CAS  Google Scholar 

  32. B. Zhao, Y. Xu, M. Ma, W. Kan, Q. Deng, Res. Chem. Intermed. 41, 8031 (2015)

    CAS  Google Scholar 

  33. J. Ye, J. Xiong, R. Sun, Carbohydr. Polym. 88, 1420 (2012)

    CAS  Google Scholar 

  34. W. Jiang, Q. Fu, H. Fan, W. Wang, Chem. Commun. 259 (2008)

  35. A. Jasiński, M. Guziński, G. Lisak, J. Bobacka, M. Bocheńska, Sensor. Actuat. B-Chem. 218, 25 (2015)

    Google Scholar 

  36. Z.-G. Wang, X.-J. Ding, Y.-Y. Huang, X.-J. Yan, B. Ding, Q.-Z. Li, C.-Z. Xie, J.-Y. Xu, Dyes Pigments 175, 108156 (2020)

    CAS  Google Scholar 

  37. Y. Zhang, L. Li, J. Wang, L. Jia, R. Yang, X. Guo, Spectrochim. Acta, Part A 230, 118030 (2020)

    CAS  Google Scholar 

  38. C. Baslak, A.N. Kursunlu, Photochem. Photobiol. Sci. 17, 1091 (2018)

    CAS  PubMed  Google Scholar 

  39. Z. Xu, P. Deng, J. Li, S. Tang, Sensor. Actuat. B-Chem. 255, 2095 (2018)

    CAS  Google Scholar 

  40. Y. Chen, N. Xie, J. Photochem. Photobiol. A. 179, 320 (2006)

    CAS  Google Scholar 

  41. D. Zhang, Z. Zang, X. Zhou, Y. Zhou, X. Tang, R. Wei, W. Liu, Inorg. Chem. Commun. 12, 1154 (2009)

    CAS  Google Scholar 

  42. T.S. Singh, P.C. Paul, H.A.R. Pramanik, Spectrochim. Acta Part A 121, 520 (2014)

    CAS  Google Scholar 

  43. J. Bu, H. Duan, X. Wang, Res. Chem. Intermed. 40, 3119 (2014)

    CAS  Google Scholar 

  44. G. He, X. Hua, N. Yang, L. Li, J. Xu, L. Yang, Q. Wang, L. Ji, Bioorg. Chem. 91, 103176 (2019)

    CAS  PubMed  Google Scholar 

  45. F. Nouri Moghadam, M. Amirnasr, S. Meghdadi, K. Eskandari, A. Buchholz, W. Plass, Spectrochim. Acta A 207, 6 (2019)

    CAS  Google Scholar 

  46. X.-Y. Xue, D.-Y. Jiang, C. Feng, H. Zhang, Z.-F. Wang, H. Zhao, Inorg. Chem. Commun. 86, 258 (2017)

    CAS  Google Scholar 

  47. Z. Li, Y. Zhou, K. Yin, Z. Yu, Y. Li, J. Ren, Dyes Pigments 105, 7 (2014)

    CAS  Google Scholar 

  48. S. Pathak, D. Das, A. Kundu, S. Maity, N. Guchhait, A. Pramanik, RSC Adv. 5, 17308 (2015)

    CAS  Google Scholar 

  49. S. Joshi, S. Kumari, A. Sarmah, D.D. Pant, R. Sakhuja, J. Mol. Liq. 248, 668 (2017)

    CAS  Google Scholar 

  50. O. Younis, E.A. Orabi, A.M. Kamal, M. Sayed, R. Hassanien, R.L. Davis, O. Tsutsumi, M. Ahmed, Opt. Mater. 100, 109713 (2020)

    CAS  Google Scholar 

  51. S. Rattanopas, P. Piyanuch, K. Wisansin, A. Charoenpanich, J. Sirirak, W. Phutdhawong, N. Wanichacheva, J. Photochem. Photobiol. A 377, 138 (2019)

    CAS  Google Scholar 

  52. S. Meghdadi, N. Khodaverdian, A. Amirnasr, P.J. French, M.E. van Royen, E.A.C. Wiemer, M. Amirnasr, J. Photochem. Photobiol. A 389, 112193 (2020)

    CAS  Google Scholar 

  53. Y.R. Bhorge, H.-T. Tsai, K.-F. Huang, A.J. Pape, S.N. Janaki, Y.-P. Yen, Spectrochim. Acta Part A 130, 7 (2014)

    CAS  Google Scholar 

  54. X. Wang, T. Xu, H. Duan, Sensor. Actuat. B-Chem. 214, 138 (2015)

    CAS  Google Scholar 

  55. M. Hosseini, A. Ghafarloo, M.R. Ganjali, F. Faridbod, P. Norouzi, M.S. Niasari, Sensor. Actuat. B-Chem. 198, 411 (2014)

    CAS  Google Scholar 

  56. D. Melton, D. VanDerveer, R. Hancock, Inorg. Chem. 4, 9306 (2006)

    Google Scholar 

  57. H.A. Benesi, J.H. Hildebrand, J. Am. Chem. Soc. 71, 2703 (1949)

    CAS  Google Scholar 

  58. T. Xu, H. Duan, X. Wang, X. Meng, J. Bu, Spectrochim. Acta Part A 138, 603 (2015)

    CAS  Google Scholar 

  59. H. Li, Q. Yao, J. Fan, J. Du, J. Wang, X. Peng, Dyes Pigments 133, 79 (2016)

    CAS  Google Scholar 

  60. J. Dong, Y. Liu, J. Hu, H. Baigude, H. Zhang, Sensor. Actuat. B-Chem. 255, 952 (2018)

    CAS  Google Scholar 

  61. J. Liu, X. Meng, H. Duan, T. Xu, Z. Ding, Y. Liu, L. Lucia, Sensor. Actuat. B-Chem. 227, 296 (2016)

    CAS  Google Scholar 

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Acknowledgements

This work was supported by Shandong Provincial Natural Science Foundation, China (No. ZR2017LC005 and ZR2016EMM13), and the Young Science Foundation of Shandong Academy of Sciences (No. 2020QN0018).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Qilu University of Technology (Shandong Academy of Sciences), Jinan, 250353, China

    Xia Meng & Hongdong Duan

  2. Chemical Technology Academy of Shandong Province, Jinan, 250014, Shandong Province, China

    Yunge Zhai

  3. Engineering Research Center of Zebrafish Models for Human Diseases and Drug Screening of Shandong Province, Biology Institute, Qilu University of Technology (Shandong Academy of Sciences), Jinan, 250014, Shandong Province, China

    Lizhen Wang

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  1. Xia Meng
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Meng, X., Wang, L., Zhai, Y. et al. Electron-donating methoxy group enhances the stability and efficiency of indole-based fluorescent probe for detecting Cu2+. Res Chem Intermed 46, 5517–5533 (2020). https://doi.org/10.1007/s11164-020-04275-9

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