Citation: Jie Pan, Wei Lin, Fang Bao, Qinglong Qiao, Guixin Zhang, Yao Lu, Zhaochao Xu. Multiple fluorescence color transitions mediated by anion-π interactions and C-F covalent bond formation[J]. Chinese Chemical Letters, ;2023, 34(2): 107519. doi: 10.1016/j.cclet.2022.05.033 shu

Multiple fluorescence color transitions mediated by anion-π interactions and C-F covalent bond formation

Jie Pan ^a ,
Wei Lin ^b ,
Fang Bao ^{a, c} ,
Qinglong Qiao ^a ,
Guixin Zhang ^{c, *,} ,
Yao Lu ^{a, *,} ,
Zhaochao Xu ^{a, *,}

a.
CAS Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
b.
China Department of Obstetrics and Gynecology, The Affiliated Hospital of Qingdao University, Qingdao 266000, China
c.
General Surgery Department, The First Affiliated Hospital of Dalian Medical University, Dalian 116011, China

zgx0109@yeah.net

luyao@dicp.ac.cn

zcxu@dicp.ac.cn

Received Date: 25 January 2022
Revised Date: 6 May 2022
Accepted Date: 10 May 2022
Available Online: 14 May 2022

Figures(3)

The emission changes of fluorescent dyes under the influence of environmental changes or interaction with analytes are the basis for designing ratiometric fluorescent probes and logic gates. However, it is rare that only one external stimulus induces continuous fluorescent color changes in a fluorescent dye. In this paper, we report a cage-like molecule formed by two benzene rings and three imidazolium salts which produces continuous fluorescence wavelength changes when interacted with fluoride ions. Fluoride ions are first bound to the center of the cage under the action of anion-π interaction, and the (C−H)⁺···F^– type ionic hydrogen bonds induce the blue-shift of fluorescence. The subsequent formation of C-F covalent bonds with fluoride ions makes the fluorophore wavelength continue to blue-shift, and finally obtains continuous multiple fluorescence changes caused by a single external stimulus. According to the fluorescence wavelength and intensity, six different fluorescence signal channels can be obtained, which can be encoded as six numbers from 0 to 5. We expect that this reaction process can find applications in quantitative anion recognition and molecular counters.
- Anion-π,
- Imidazolium,
- C-F bond,
- Miltple color,
- Fluorescent probe
1. [1]
  C. Wang, W. Chi, Q. Qiao, et al., Chem. Soc. Rev. 50 (2021) 12656–12678. doi: 10.1039/D1CS00239B
2. [2]
  X. Liu, Q. Qiao, W. Tian, et al., J. Am. Chem. Soc. 138 (2016) 6960–6963. doi: 10.1021/jacs.6b03924
3. [3]
  W. Zhou, X. Fang, Q. Qiao, et al., Chin. Chem. Lett. 32 (2021) 943–946. doi: 10.1016/j.cclet.2021.02.003
4. [4]
  Z. Xu, Coord. Chem. Rev. 444 (2021) 214036. doi: 10.1016/j.ccr.2021.214036
5. [5]
  W. Liu, L. Miao, X. Li, Z. Xu, Coord. Chem. Rev. 429 (2021) 213646. doi: 10.1016/j.ccr.2020.213646
6. [6]
  W. Liu, J. Chen, Z. Xu, Coord. Chem. Rev. 429 (2021) 213638. doi: 10.1016/j.ccr.2020.213638
7. [7]
  C. Wang, Q. Qiao, W. Chi, et al., Angew. Chem. Int. Ed. 59 (2020) 10160–10172. doi: 10.1002/anie.201916357
8. [8]
  J. Chen, C. Wang, W. Liu, et al., Angew. Chem. Int. Ed. 60 (2021) 25104–25113. doi: 10.1002/anie.202111052
9. [9]
  Q. Qi, S. Jiang, Q. Qiao, et al., Chin. Chem. Lett. 31 (2020) 2985–2987. doi: 10.1016/j.cclet.2020.05.044
10. [10]
  W. Chi, Q. Qiao, C. Wang, et al., Angew. Chem. Int. Ed. 59 (2020) 20215–20223. doi: 10.1002/anie.202010169
11. [11]
  W. Chi, J. Chen, W. Liu, et al., J. Am. Chem. Soc. 142 (2020) 6777–6785. doi: 10.1021/jacs.0c01473
12. [12]
  W. Liu, R. Li, F. Deng, et al., ACS Appl. Bio Mater. 4 (2021) 2104–2112. doi: 10.1021/acsabm.0c01269
13. [13]
  X. Fang, W. Liu, X. Wu, et al., Results Chem. 3 (2021) 100092. doi: 10.1016/j.rechem.2020.100092
14. [14]
  S. Kou, H.N. Lee, D. van Noort, et al., Angew. Chem. Int. Ed. 47 (2008) 872–876. doi: 10.1002/anie.200703813
15. [15]
  F. Deng, Z. Xu, Chin. Chem. Lett. 30 (2019) 1667–1681. doi: 10.1016/j.cclet.2018.12.012
16. [16]
  S. Long, W. Chi, L. Miao, et al., Chin. Chem. Lett. 30 (2019) 601–604. doi: 10.1016/j.cclet.2018.12.008
17. [17]
  S. Long, L. Miao, R. Li, et al., ACS Sens. 4 (2019) 281–285. doi: 10.1021/acssensors.8b01466
18. [18]
  X. Li, J. Zheng, W. Liu, et al., Chin. Chem. Lett. 31 (2020) 2937–2940. doi: 10.1016/j.cclet.2020.05.043
19. [19]
  Q. Qi, W. Chi, Y. Li, et al., Chem. Sci. 10 (2019) 4914–4922. doi: 10.1039/C9SC01284B
20. [20]
  F. Deng, Q. Qiao, J. Li, et al., J. Phys. Chem. B 124 (2020) 7467–7474. doi: 10.1021/acs.jpcb.0c05642
21. [21]
  B.L. Schottel, H.T. Chifotides, K.R. Dunbar, Chem. Soc. Rev. 37 (2008) 68–83. doi: 10.1039/B614208G
22. [22]
  D.X. Wang, M.X. Wang, J. Am. Chem. Soc. 135 (2013) 892–897. doi: 10.1021/ja310834w
23. [23]
  I.A. Rather, S.A. Wagay, R. Ali, Coord. Chem. Rev. 415 (2020) 213327. doi: 10.1016/j.ccr.2020.213327
24. [24]
  Z. Xu, N.J. Singh, S.K. Kim, et al., Chem. Eur. J. 17 (2011) 1163–1170. doi: 10.1002/chem.201002105
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