An Intramolecular Charge Transfer (ICT)-Based Fluorescent Probe of Hydrogen Sulphide under pH Control Strategy

  • Zhu Jihua ,
  • Zhang Hao ,
  • Liu Min ,
  • Liu Jingjiang ,
  • Liao Yuan ,
  • Quan Zhengjun ,
  • Wang Xicun
Expand
  • a College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070;
    b College of Chemistry and Chemical Engineering, Longdong University, Qingyang, Gansu 745000

Received date: 2019-10-20

  Revised date: 2019-11-12

  Online published: 2020-05-06

Supported by

Project supported by the Longyuan Youth Innovative and Entrepreneurial Talents Project (No. 2019-39) and the Research Project of Higher Education in Gansu Province (No. 2018A-004).

Abstract

Hydrogen sulfide (H2S) and pH play a most important role in vivo and environment. A fluorescent probe for fast and sensitive detection of H2S and pH are of vital importance for research their functions. A naphthalimide-based fluorescent probe L has been designed and synthesized based on intramolecular charge transfer (ICT) mechanism by utilizing azide as recognition site. The probe L has demonstrated good stability in the pH range of 4~11. It showed satisfactory sensitivity and rapidly response (less than 3 min) to H2S. An excellent linear relationship (R2=0.99823) displayed in the range of H2S concentrations from 0 μmol·L-1 to 20 μmol·L-1 and the detection limit was 1.18 μmol·L-1. Furthermore, in the present 30 equiv. H2S, it was successfully applied to detection of pH with good linear relationship (R2=0.98764) in the pH range of 2~6.5. This methods provide a reference for detection of H2S and pH value in the presence of 30 equiv. H2S, which have potential application prospects in analytical detection and pathological analysis.

Cite this article

Zhu Jihua , Zhang Hao , Liu Min , Liu Jingjiang , Liao Yuan , Quan Zhengjun , Wang Xicun . An Intramolecular Charge Transfer (ICT)-Based Fluorescent Probe of Hydrogen Sulphide under pH Control Strategy[J]. Chinese Journal of Organic Chemistry, 2020 , 40(4) : 1043 -1049 . DOI: 10.6023/cjoc201910024

References

[1] Sjaastad, O.; Bakketeig, L. S. Cephalalgia 2006, 26, 466.
[2] Szabó, C. Nat. Rev. Drug Discovery 2007, 6, 917.
[3] Kaushik, R.; Ghosh, A.; Jose D. A. Coord. Chem. Rev. 2017, 347, 141.
[4] Zhou, C.; Qiu, B.; Zeng, Y.; Chen, J. P.; Yu, T. J.; Li, Y. Chin. J. Org. Chem. 2017, 37, 92(in Chinese). (周婵, 邱波, 曾毅, 陈金平, 于天君, 李嫕, 有机化学, 2017, 37, 92.)
[5] Sun, L.; Wu, Y.; Chen, J.; Zhong, J.; Zeng, F.; Wu, S. Theranostics 2019, 9, 77.
[6] Abe, K.; Kimura, H. J. Neurosci. 1996, 16, 1066.
[7] Yang, G.; Wu, L.; Jiang, B.; Yang, W.; Qi, J.; Cao, K.; Zhang, S. Science 2008, 322, 587.
[8] Lavu, M.; Bhushan, S.; Lefer, D. J. Clin. Sci. 2011, 120, 219.
[9] de Sousa, M. C.; Vieira, R. B.; Dos Santos, D. S.; Carvalho, C. A.; Camargo, S. E.; Mancini, M. N.; de Oliveira, L. D. Arch. Oral Biol. 2015, 60, 600.
[10] Shi, W.; Pan, M.; Qiang, H.; Qiu, Q.; Huang, W.; Lin, H.; Qian, H.; Ge, L. Chem. Biol. Drug Des. 2017, 90, 167.
[11] Li, X.; Liu, Q.; Ye, S.; Wang, S.; Li, K.; Lv, G.; Peng, Y.; Qiu, L.; Lin, J. Chem. Biol. Drug Des. 2019, 94, 1494.
[12] Eto, K.; Asada, T.; Arima, K.; Makifuchi, T.; Kimura, H. Biochem. Biophys. Res. Commun. 2002, 293, 1485.
[13] Wang, H.; Yang, D.; Tan, R.; Zhou, Z. J.; Xu, R.; Zhang, J. F. Zhou, Y. Sens. Actuators, B 2017, 247, 883.
[14] Shi, D. T.; Zhou, D.; Zang, Y.; Li J.; Chen, G. R.; James, T. D.; He, X. P.; Tian, H. Chem. Commun. 2015, 51, 3653.
[15] Chen, S.; Ma, C.; Wang, D.-E.; Han, X.; Zhang, L.; Wang, J. Anal. Methods 2015, 7, 7646.
[16] Feng, X.; Zhang, T.; Liu, J.-T.; Miao, J.-Y.; Zhao, B.-X. Chem. Commun. 2016, 52, 3131.
[17] Cao, D.; Liu, Z.; Verwilst, P.; Koo, S.; Jangjili, P.; Kim, J. S.; Lin, W. Chem. Rev. 2019, 119, 10403.
[18] Peng, H.; Cheng, Y.; Dai, C.; King, A. L.; Predmore, B. L.; Lefer, D. J.; Wang, B. Angew. Chem., Int. Ed. 2011, 50, 9672.
[19] He, P.; Tang, L.-J; Zhong, K.-L.; Hou, S.-H.; Yan, X.-M. Chin. J. Org. Chem. 2017, 37, 423(in Chinese). (何平, 汤立军, 钟克利, 侯淑华, 燕小梅, 有机化学, 2017, 37, 423.)
[20] Wang, H.; Wu, X.-M.; Yang, S.-X.; Tian, H.-Y.; Liu, Y.-G.; Sun, B.-G. Dyes Pigm. 2019, 160, 757.
[21] Renault, K.; Renard, P.-Y.; Sabot, C. New J. Chem. 2017, 41, 10432.
[22] Li, H.; Feng, X.; Guo, Y.; Chen, D.; Li, R.; Ren, X. Sci. Rep. 2014, 4, 4366.
[23] Jun, M. E.; Roy, B.; Ahn, K. H. Chem. Commun. 2011, 47, 7583.
[24] Chen, H.; Gong, X.; Liu, X.; Li, Z.; Zhang, J.; Yang, X.-F. Sens. Actuators, B 2019, 281, 542.
[25] Chen, Y.; Zhu, C.; Yang, Z. Chen, J.; He, Y.; Jiao, Y. Angew. Chem., Int. Ed. 2013, 52, 1688.
[26] Lippert, R.; New, E. L.; Chang, C. J. J. Am. Chem. Soc. 2011, 133, 10078.
[27] Lippert, A. R. J. Inorg. Biochem. 2014, 133, 136.
[28] Platt, F. M. Nature. 2014, 510, 68.
[29] Liu, X.; Su, Y.; Tian, H.; Yang, L.; Zhang, H.; Song, X.; Foley, J. W. Anal. Chem. 2017, 89, 7038.
[30] Xue, Z.; Zhao, H.; Liu, J.; Han, J.; Han, S. ACS Sens. 2017, 2, 436.
[31] Sun, T.; Xia, L.; Huang, J.; Gu, Y.; Wang, P. Talanta 2018, 187, 295.
[32] Fan, F.; Jing, J.; Chen, X. Chin. J. Org. Chem. 2014, 34, 2178(in Chinese). (范方禄, 靖金球, 陈雪梅, 有机化学, 2014, 34, 2178.)
[33] Peng, S.; Zhong, T.; Guo, T.; Shu, D.; Meng, D.; Liu, H.; Guo, D. New J. Chem. 2018, 42, 5185.
[34] Pancholi, J.; Hodson, D. J.; Jobe, K.; Rutter, G. A.; Goldup, S. M.; Watkinson, M. Chem. Sci. 2014, 5, 3528.
Outlines

/