SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2024 , Vol. 44 >Issue 9: 2869 - 2875

DOI: https://doi.org/10.6023/cjoc202402010

ARTICLES

Synthesis of Two-Photon Dansyl-Based Fluorescent Probe with Dual-State Emission Properties for Hydrogen Sulfide Detection

  • Chun He ,
  • Shuqi Liu ,
  • Fenmin Cheng ,
  • Yuanqiang Hao ,
  • Shu Chen ,
  • Peisheng Zhang ,
  • Rongjin Zeng
Expand
  • School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201
* ;

Received date: 2024-02-20

  Revised date: 2024-04-10

  Online published: 2024-05-11

Supported by

National Natural Science Foundation of China(52273290); National Natural Science Foundation of China(52173278); National Natural Science Foundation of China(52073087); Natural Science Foundation of Hunan Province(2024JJ2033); Science and Technology Innovation Program of Hunan Province(2022RC1075)

Fold

Abstract

Hydrogen sulfide (H2S) is a kind of irritant and volatile environmental toxic gas. It is also an important functional small molecule in organisms. Therefore, it is very important to develop fluorescent probes that can detect H2S in different states (such as solution and gas). In this study, a dansyl-based fluorophore (DNs) with dual-state emission (DSE) properties and high fluorescence quantum yields was successfully synthesized. Furthermore, a 2,4-dinitrobenzenesulfonyl moiety was introduced to synthesize a fluorescent probe, DNs-HPP-DNBS, for H2S detection. Leveraging the DSE properties of DNs, the DNs-HPP-DNBS probe not only achieved sensitive detection of H2S in solution, with a detection limit of 1.16 μmol•L－1. At the same time, it can monitor gaseous H2S after loading on solid substrate. In addition, its two-photon performance is expected to play its good application potential in biology and cell imaging.

Key words： dual-state emission; two-photon; fluorescent probe; hydrogen sulfide

Cite this article

Chun He , Shuqi Liu , Fenmin Cheng , Yuanqiang Hao , Shu Chen , Peisheng Zhang , Rongjin Zeng . Synthesis of Two-Photon Dansyl-Based Fluorescent Probe with Dual-State Emission Properties for Hydrogen Sulfide Detection[J]. Chinese Journal of Organic Chemistry, 2024 , 44(9) : 2869 -2875 . DOI: 10.6023/cjoc202402010

References

[1]
Cheng, D.; Peng, J.; Yuan, L.; Lv, Y.; Su, D.; Liu, D.; Chen, M.; Yuan, L.; Zhang, X. J. Am. Chem. Soc. 2019, 141, 6352.
[2]
Jimenez, D.; Martínez-Má?ez, R.; Sancenon, F.; Ros-Lis, J.; Benito, A.; Soto, J. J. Am. Chem. Soc. 2003, 125, 9000.,
[3]
Coavoy-Sánchez, S. A.; Costa, S. K. P.; Muscará, M. N. Br. J. Pharmacol. 2020, 177, 857.
[4]
Sun, M.; Yu, H.; Li, H.; Xu, H.; Huang, D.; Wang, S. Inorg. Chem. 2015, 54, 3766.
[5]
Szabo?, C. Nat. Rev. Drug Discovery 2007, 6, 917.
[6]
Zhou, L.; Chen, Y.; Shao, B.; Cheng, J.; Li, X. Front. Chem. Sci. Eng. 2022, 16, 34.
[7]
Kong, F.; Wang, X.; Bai, J.; Li, X.; Yang, C.; Li, Y.; Xu, K.; Tang, B. Chem. Commun. 2021, 57, 6604.
[8]
Cheng, S.; Zhang, L.; Zhang, M. Electroanal. 2022, 34, 1027.
[9]
Jia, X.; Li, W.; Guo, Z.; Guo, Z.; Li, Y.; Zhang, P.; Wei, C.; Li, X. ChemistrySelect 2019, 4, 8671.
[10]
Zhang, Q.; Yang, Z.; Zhou, H.; Du, J.; Shang, H. Microchim. Acta 2023, 190, 474.
[11]
Shang, H.; Dong, S.; Zhang, X.; Zhang, A.; Du, J. ACS Appl. Nano Mater. 2023, 6, 23576.
[12]
Ahn, B.; Ahn, Y.; Lee, Y.; Lee, Y.; Lee, G. Sensors 2022, 22, 5928.
[13]
Wronski, M. Anal. Chem. 1971, 43, 606.
[14]
Sarkar, S.; Ha, Y.; Soni, N.; An, G.; Lee, W.; Kim, M.; Huynh, P.; Ahn, H.; Bhatt, N.; Lee, Y.; Kim, J.; Park, K.; Ishii, I.; Kang, S.; Yoo, J. Angew. Chem., Int. Ed. 2016, 55, 9365.
[15]
Colon, M.; Todoli, J. L.; Hidalgo, M.; Iglesias, M. Anal. Chim. Acta 2008, 609, 160.
[16]
Ma, F.; Sun, M.; Zhang, K.; Yu, H.; Wang, Z.; Wang, S. Anal. Chim. Acta 2015, 879, 104.
[17]
Chen, L.; Wu, D.; Lim, C. S.; Nam, S.; Lee, W.; Kim, G.; Kim, H. M.; Yoon, J. Chem. Commun. 2017, 53, 4791.
[18]
F?rster, T. Angew. Chem., nt. Ed. 1969, 8, 333.
[19]
Choi, H.; Lim, C; Cho, M.; Kang, J.; Park, S.; Kim, H. Sens. Actuators, B 2019, 283, 810.
[20]
Li, L.; Li, W.; Zheng, J.; Chen, H.; Yuan, Z. Biomater. Sci. 2020, 8, 224.
[21]
Luo, J.; Xie, Z.; Lam, J.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Chem. Commun. 2001, 1740.
[22]
Chen, L.; Wu, D.; Lim, C.; Kim, D.; Nam, S.; Lee, W.; Kim, G.; Kim, H.; Yoon, J. Chem. Commun. 2017, 53, 4791.
[23]
Zhou, C.; Wang, M.; Guo, W.; Ye, G.; Wang, Y.; Yang, Y.; Xia, G.; Wang, H. Dyes Pigm. 2023, 213, 111198.
[24]
Xu, C.; Li, T.; Miao, J.; Liu, K.; Nie, Y.; Liu, G.; Jiang, X. New J. Chem. 2023, 47, 4448.
[25]
Lim, C.; Das, S.; Yang, S.; Kim, E.; Chun, H.; Cho, B. Anal. Chem. 2013, 85, 9288.
[26]
Zeng, L.; Chen, S.; Xia, T.; Hu, W.; Li, C.; Liu, Z. Anal. Chem. 2015, 87, 3004.
[27]
Ma, Q.; Xu, J.; Zhang, X.; Zhou, X.; Zhou, L.; Liu, H.; Zhang, J. Sens. Actuators, B 2016, 229, 434.
[28]
Jeong, E.; Yoon, S.; Lee, H. S.; Kumar, A.; Chae, P. S. Dyes Pigm. 2019, 162, 348.
[29]
Wang, Y.; Zhou, J.; Zhao, L.; Xu, B. Dyes Pigm. 2020, 18, 10851.
[30]
Sha, C.; Li, Z.; Lu, S.; Hu, X.; Xu, D. Res. Chem. Intermed. 2022, 48, 5227.
[31]
Sha, C.; Lu, S.; Lv, F.; Xu, D. Res. Chem. Intermed. 2016, 42, 5825.
[32]
Wang, Y.; Zeng, L.; Zhou, J.; Jiang, B.; Zhao, L.; Wang, C.; Xu, B. Spectrochim. Acta A 2019, 223, 117348.
[33]
Liu, Y.; Wang, Y.; Xu, B. J. Fluoresc. 2022, 32, 227.
[34]
Portillo Moreno, O.; Palomino Merino, R.; Hernández-Téllez, G.; Gutiérrez Argüelles, D.; Meléndez Bustamante, F.; Mendoza, A.; Rubio Rosas, E.; Gutiérrez Pérez, R. Opt. Mater. 2018, 84, 646.
[35]
Yu, C.; Wang, S.; Xu, C.; Ding, Y.; Zhang, G.; Yang, N.; Wu, Q.; Xiao, Q.; Wang, L.; Fang, B.; Pu, C.; Ge, J.; Gao, L.; Li, L.; Yao, S. Adv. Healthcare Mater. 2022, 11, 2200400.
Options
Outlines

/

〈 〉