Citation: Zhu Junlong, Jia Peipei, Li Nuo, Tan Shaoying, Huang Junhai, Xu Lin. Small-molecule fluorescent probes for the detection of carbon dioxide[J]. Chinese Chemical Letters, ;2018, 29(10): 1445-1450. doi: 10.1016/j.cclet.2018.09.002 shu

Small-molecule fluorescent probes for the detection of carbon dioxide

Zhu Junlong ^a ,
Jia Peipei ^a ,
Li Nuo ^a ,
Tan Shaoying ^b ,
Huang Junhai ^b,, ,
Xu Lin ^a,,

a.
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062, China
b.
Zhangjiang Institute, China State Institute of Pharmaceutical Industry, Shanghai 201203, China

Corresponding author: Huang Junhai, huang_junhai@163.com Xu Lin, lxu@chem.ecnu.edu.cn
Received Date: 16 August 2018
Revised Date: 5 September 2018
Accepted Date: 5 September 2018
Available Online: 6 October 2018

Figures(18)

During the last few years, the preparation of novel fluorescent probes for the detection of carbon dioxide has attracted considerable attention since carbon dioxide plays extremely important roles in widespread fields including chemical, environmental, clinical analysis, and agri-food industry. This review focuses on the recent advances in the design principles, recognition mechanisms, and preparation of small-molecule fluorescent probes for the selective detection and monitoring of CO₂. Moreover, their properties and functions will be discussed detailedly as well.
- Fluorescent probe,
- Carbon dioxide,
- Design principle,
- Sensing mechanism
1. [1]
  D. Chen, H. Wang, L. Dong, et al., Biomaterials 103(2016) 67-74. doi: 10.1016/j.biomaterials.2016.06.055
2. [2]
  J. Sun, B. Ye, G. Xia, X. Zhao, H. Wang, Sens. Actuators B 233(2016) 76-82. doi: 10.1016/j.snb.2016.04.052
3. [3]
  L.H. Yang, H.M. Wang, ChemSusChem 7(2014) 962-998. doi: 10.1002/cssc.201301131
4. [4]
  C. Ziebart, C. Federsel, P. Anbarasan, et al., J. Am. Chem. Soc.134(2012) 20701-20704. doi: 10.1021/ja307924a
5. [5]
  C. Finn, S. Schnittger, L.J. Yellowlees, J.B. Love, Chem. Commun. 48(2012) 1392-1399. doi: 10.1039/C1CC15393E
6. [6]
  O. Alduhaish, B. Li, H. Arman, et al., Chin. Chem. Lett. 28(2017) 1653-1658. doi: 10.1016/j.cclet.2017.04.025
7. [7]
  M.X. Wu, Y.W. Yang, Chin. Chem. Lett. 28(2017) 1135-1143. doi: 10.1016/j.cclet.2017.03.026
8. [8]
  F.Q. Meng, X.J. Feng, W.H. Wang, M. Bao, Chin. Chem. Lett. 28(2017) 900-904. doi: 10.1016/j.cclet.2016.12.018
9. [9]
  C.M. Kenific, J. Debnath, Trends Cell Biol. 25(2015) 37-45. doi: 10.1016/j.tcb.2014.09.001
10. [10]
  C. Descoins, M. Mathlouthi, M.L. Moual, J. Hennequin, J. Food Chem. 95(2006) 541-553. doi: 10.1016/j.foodchem.2004.11.031
11. [11]
  L.A. Blanchard, J.F. Brennecke, Ind. Eng. Chem. Res. 40(2001) 287-292. doi: 10.1021/ie000710d
12. [12]
  O.S. Wolfbeis, L.J. Weis, M.J.P. Leiner, W.E. Ziegler, Anal. Chem. 60(1988) 2028-2030. doi: 10.1021/ac00170a009
13. [13]
  R.V. Geldern, M.E. Nowak, M. Zimmer, et al., Anal. Chem. 86(2014) 12191-12198. doi: 10.1021/ac5031732
14. [14]
  J.J. Gassensmith, J.Y. Kim, J.M. Holcroft, et al., J. Am. Chem. Soc. 136(2014) 8277-8282. doi: 10.1021/ja5006465
15. [15]
  T. Tian, X. Chen, H. Li, et al., Analyst 138(2013) 991-994. doi: 10.1039/C2AN36401H
16. [16]
  L.Q. Xu, B. Zhang, M. Sun, et al., J. Mater. Chem. A 1(2013) 1207-1212. doi: 10.1039/C2TA00482H
17. [17]
  R.N. Dansby-Sparks, J. Jin, S.J. Mechery, et al., Anal. Chem. 82(2010) 593-600. doi: 10.1021/ac901890r
18. [18]
  M. Ishida, P. Kim, J. Choi, et al., Chem. Commun. 49(2013) 6950-6952. doi: 10.1039/c3cc43938k
19. [19]
  W. Zheng, L.J. Chen, G. Yang, et al., J. Am. Chem. Soc. 138(2016) 4927-4937. doi: 10.1021/jacs.6b01089
20. [20]
  S. Pandey, S.N. Baker, S. Pandey, G.A. Baker, Chem. Commun. 48(2012) 7043-7045. doi: 10.1039/c2cc32164e
21. [21]
  B. Jiang, J. Zhang, J.Q. Ma, et al., J. Am. Chem. Soc. 138(2016) 738-741. doi: 10.1021/jacs.5b11409
22. [22]
  B. Sun, M. Wang, Z. Lou, et al., J. Am. Chem. Soc. 137(2015) 1556-1564. doi: 10.1021/ja511443p
23. [23]
  Y. Chen, T. Wei, Z. Zhang, et al., Chin. Chem. Lett. 28(2017) 1957-1960. doi: 10.1016/j.cclet.2017.05.010
24. [24]
  M. Lee, J.H. Moon, K.M.K. Swamy, et al., Sens. Actuators B 199(2014) 369-376. doi: 10.1016/j.snb.2014.04.005
25. [25]
  Z.H. Pan, G.G. Luo, J.W. Zhou, et al., Dalton Trans. 43(2014) 8499-8507. doi: 10.1039/C4DT00395K
26. [26]
  R. Ali, S.S. Razi, R.C. Gupta, S.K. Dwivedi, A. Misra, New J. Chem. 40(2016) 162-170. doi: 10.1039/C5NJ01920F
27. [27]
  S. Schutting, S.M. Borisov, I. Klimant, Anal. Chem. 85(2013) 3271-3279. doi: 10.1021/ac303595v
28. [28]
  D.G. Khandare, H. Joshi, M. Banerjee, M.S. Majik, A. Chatterjee, Anal. Chem. 87(2015) 10871-10877. doi: 10.1021/acs.analchem.5b02339
29. [29]
  X. Zhang, S. Lee, Y. Liu, et al., Sci. Rep. 4(2014) 4593-4600.
30. [30]
  Q. Xu, S. Lee, Y. Cho, et al., J. Am. Chem. Soc. 135(2013) 17751-17754. doi: 10.1021/ja410557x
31. [31]
  X. Zhou, S. Lee, Z. Xu, J. Yoon, Chem. Rev. 115(2015) 7944-8000. doi: 10.1021/cr500567r
32. [32]
  Y. Hong, J.W.Y. Lam, B.Z. Tang, Chem. Soc. Rev. 40(2011) 5361-5388. doi: 10.1039/c1cs15113d
33. [33]
  J. Luo, Z. Xie, J.W.Y. Lam, et al., Chem. Commun. (2001) 1740-1741.
34. [34]
  L.J. Chen, Y.Y. Ren, N.W. Wu, et al., J. Am. Chem. Soc. 137(2015) 11725-11735. doi: 10.1021/jacs.5b06565
35. [35]
  Y. Liu, Y. Tang, N.N. Barashkov, et al., J. Am. Chem. Soc. 132(2010) 13951-13953. doi: 10.1021/ja103947j
36. [36]
  H. Wang, D. Chen, Y. Zhang, et al., J. Mater. Chem. C 3(2015) 7621-7626. doi: 10.1039/C5TC01280E
37. [37]
  S.N. Riduan, Y. Zhang, J.Y. Ying, Angew. Chem. Int. Ed. 48(2009) 3322-3325. doi: 10.1002/anie.v48:18
38. [38]
  Z. Guo, N.R. Song, J.H. Moon, et al., J. Am. Chem. Soc. 134(2012) 17846-17849. doi: 10.1021/ja306891c
39. [39]
  M. Lee, S. Jo, D. Lee, Z. Xu, J. Yoon, Dyes Pigm. 120(2015) 288-292. doi: 10.1016/j.dyepig.2015.04.029
40. [40]
  R. Ali, S.S. Razi, M. Shahid, P. Srivastava, A. Misra, Spectrochim. Acta Part A 168(2016) 21-28. doi: 10.1016/j.saa.2016.05.045
41. [41]
  A.H. Liu, R. Ma, C. Song, et al., Angew. Chem. Int. Ed. 51(2012) 11306-11310. doi: 10.1002/anie.201205362
42. [42]
  Y. Zhang, S. Zhang, X. Lu, et al., Chem.-Eur. J. 15(2009) 3003-3011. doi: 10.1002/chem.v15:12
43. [43]
  W. Zheng, G. Yang, N. Shao, et al., J. Am. Chem. Soc. 139(2017) 13811-13820. doi: 10.1021/jacs.7b07303
44. [44]
  S. Kang, J. Kim, J.H. Park, et al., Dyes Pigm. 123(2015) 125-131. doi: 10.1016/j.dyepig.2015.07.033
45. [45]
  Z. Xu, J. Chen, L.L. Hua, et al., Chin. Chem. Lett. 28(2017) 1935-1942. doi: 10.1016/j.cclet.2017.07.018
46. [46]
  P. Zhang, Z.Q. Guo, C.X. Yan, W.H. Zhu, Chin. Chem. Lett. 28(2017) 1952-1956. doi: 10.1016/j.cclet.2017.08.038
47. [47]
  M.L. He, S. Wu, J. He, Z. Abliz, L. Xu, RSC Adv. 4(2014) 2605-2608. doi: 10.1039/C3RA46500D
48. [48]
  C.B. Huang, J. Huang, L. Xu, RSC Adv. 5(2015) 13307-13310. doi: 10.1039/C4RA08337G
49. [49]
  L. Phan, J.R. Andreatta, L.K. Horvey, et al., J. Org. Chem. 73(2008) 127-132. doi: 10.1021/jo7017697
50. [50]
  L. Song, X.D. Sun, Y. Ge, et al., Chin. Chem. Lett. 27(2016) 1776-1780. doi: 10.1016/j.cclet.2016.05.007
51. [51]
  Y. Yang, H. Wang, Y.L. Wei, et al., Chin. Chem. Lett. 28(2017) 2023-2026. doi: 10.1016/j.cclet.2017.08.051
52. [52]
  B. Jiang, L.J. Chen, Y. Zhang, et al., Chin. Chem. Lett. 27(2016) 607-612. doi: 10.1016/j.cclet.2016.03.017
53. [53]
  B. Li, Z. He, H. Zhou, H. Zhang, T. Cheng, Chin. Chem. Lett. 28(2017) 1929-1934. doi: 10.1016/j.cclet.2017.08.055
54. [54]
  T. Liu, X. Liu, D.R. Spring, et al., Sci. Rep. 4(2014) 5418-5424.
55. [55]
  L. Wang, Y. Xiao, W. Tian, L. Deng, J. Am. Chem. Soc. 135(2013) 2903-2906. doi: 10.1021/ja311688g
56. [56]
  Y.J. Jin, B.C. Moon, G. Kwak, Dyes Pigm. 132(2016) 270-273. doi: 10.1016/j.dyepig.2016.05.003
57. [57]
  C.B. Huang, L. Xu, J.L. Zhu, et al., J. Am. Chem. Soc. 139(2017) 9459-9462. doi: 10.1021/jacs.7b04659
58. [58]
  L.J. Chen, S. Chen, Y. Qin, et al., J. Am. Chem. Soc. 140(2018) 5049-5052. doi: 10.1021/jacs.8b02386
59. [59]
  H.I. Un, S. Wu, C.B. Huang, Z. Xu, L. Xu, Chem. Commun. 51(2015) 3143-3146. doi: 10.1039/C4CC09488C
60. [60]
  Z. Xu, L. Xu, Chem. Commun. 52(2016) 1094-1119. doi: 10.1039/C5CC09248E
61. [61]
  W.J. Fan, B. Sun, J. Ma, et al., Chem. Eur. J. 21(2015) 12947-12959. doi: 10.1002/chem.201501282
62. [62]
  J. Zhang, N.W. Wu, X.D. Xu, et al., RSC Adv. 4(2014) 16047-16054. doi: 10.1039/C3RA46957C
63. [63]
  H.I. Un, C.B. Huang, J. Huang, et al., Chem. Asian J. 9(2014) 3397-3402. doi: 10.1002/asia.v9.12
64. [64]
  C.B. Huang, H.R. Li, Y. Luo, L. Xu, Dalton Trans. 43(2014) 8102-8108. doi: 10.1039/c4dt00014e
65. [65]
  L. Wang, L.J. Chen, J.Q. Ma, et al., J. Organomet. Chem. 823(2016) 1-7. doi: 10.1016/j.jorganchem.2016.09.001
66. [66]
  C.B. Huang, L.J. Chen, J. Huang, L. Xu, RSC Adv. 4(2014) 19538-19549. doi: 10.1039/c4ra02373k
67. [67]
  H.I. Un, C.B. Huang, C. Huang, et al., Org. Chem. Front. 1(2014) 1083-1090. doi: 10.1039/C4QO00185K
68. [68]
  Y.Y. Ren, N.W. Wu, J. Huang, et al., Chem. Commun. 51(2015) 15153-15156. doi: 10.1039/C5CC04789G
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