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Review
. 2020 Mar 17;10(18):10826-10847.
doi: 10.1039/c9ra10290f. eCollection 2020 Mar 11.

Synthesis and application of coumarin fluorescence probes

Xiao-Ya Sun  1   2   3 , Teng Liu  4   2   3 , Jie Sun  4   2   3 , Xiao-Jing Wang  4   2   3
Affiliations
Review

Synthesis and application of coumarin fluorescence probes

Xiao-Ya Sun et al. RSC Adv. .

Abstract

In recent years, the research on fluorescent probes has developed rapidly. Coumarin fluorescent probes have also been one of the hot topics in recent years. For the synthesis and application of coumarin fluorescent probes, great progress has been made. Coumarin fluorescent probes have become more and more widely used in biochemistry, environmental protection, and disease prevention, and have broad prospects. This review introduces the three main light emitting mechanisms (PET, ICT, FRET) of fluorescent probes, and enumerates some probes based on this light emitting mechanism. In terms of the synthesis of coumarin fluorescent probes, the existing substituents on the core of coumarin compounds were modified. Based on the positions of the modified substituents, some of the fluorescent probes reported in the past ten years are listed. Most of the fluorescent probes are formed by modifying the 3 and 7 position substituents on the mother nucleus, and the 4 and 8 position substituents are relatively less modified. In terms of probe applications, the detection and application of coumarin fluorescent probes for Cu2+, Hg2+, Mg2+, Zn2+, pH, environmental polarity, and active oxygen and sulfide in the past ten years are mainly introduced.

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Conflict of interest statement

The authors declare that this article content has no conflict of interest.

Figures

Fig. 1
Fig. 1. The structure of compound 1.
Fig. 2
Fig. 2. The structure of compound 2.
Fig. 3
Fig. 3. The “fluorophore–spacer–receptor” format of fluorescent PET. (Picture from ref. 33).
Fig. 4
Fig. 4. The structure of compound 3.
Fig. 5
Fig. 5. The structure of compound 4.
Fig. 6
Fig. 6. (a) An electron transfer from the analyte-free receptor to the photo-excited fluorophore creates the “off” state of the sensor. (b) The electron transfer from the analyte-bound receptor is blocked resulting in the “on” state of the sensor. (Picture from ref. 33).
Fig. 7
Fig. 7. Molecular orbital energy diagrams (Picture from ref. 37).
Fig. 8
Fig. 8. The structure of compound 5.
Fig. 9
Fig. 9. The structure of compound 6.
Fig. 10
Fig. 10. The structure of compound 7.
Fig. 11
Fig. 11. The structure of compound 8.
Fig. 12
Fig. 12. Intramolecular conjugate charge transfer principle (Picture from ref. 43).
Fig. 13
Fig. 13. The structure of compound 9.
Fig. 14
Fig. 14. The structure of compound 10.
Fig. 15
Fig. 15. The structure of compound 11.
Fig. 16
Fig. 16. The structure of compound 12.
Fig. 17
Fig. 17. The chemical structure and numbering scheme of coumarin.
Fig. 18
Fig. 18. The synthetic route of compound 6.
Fig. 19
Fig. 19. The synthetic route of compound 18.
Fig. 20
Fig. 20. The synthetic route of compound 21.
Fig. 21
Fig. 21. The synthetic route of compound 24.
Fig. 22
Fig. 22. The synthetic route of compound 27.
Fig. 23
Fig. 23. The synthetic route of compound 29.
Fig. 24
Fig. 24. Synthesis of compound 5.
Fig. 25
Fig. 25. Synthesis of compound 35.
Fig. 26
Fig. 26. Synthesis of compound 38.
Fig. 27
Fig. 27. Synthesis of compound 40.
Fig. 28
Fig. 28. The structure of compound 41 and 42.
Fig. 29
Fig. 29. The structure of compound 43.
Fig. 30
Fig. 30. The structure of compound 44.
Fig. 31
Fig. 31. The structure of compound 45.
Fig. 32
Fig. 32. The structure of compound 46.
Fig. 33
Fig. 33. The structure of compound 47.
Fig. 34
Fig. 34. The structure of compound 48.
Fig. 35
Fig. 35. The structure of compound 49.
Fig. 36
Fig. 36. The structure of compound 50.
Fig. 37
Fig. 37. The structure of compound 51, 52.
Fig. 38
Fig. 38. The structure of compound 53.
Fig. 39
Fig. 39. The structure of compound 54.
Fig. 40
Fig. 40. The structure of compound 55.
Fig. 41
Fig. 41. The structure of compound 18.
Fig. 42
Fig. 42. The structure of compound 56.
Fig. 43
Fig. 43. The structure of compound 57.
Fig. 44
Fig. 44. The structure of compound 58.
Fig. 45
Fig. 45. The structure of compound 59.
Fig. 46
Fig. 46. The structure of compound 60.
Fig. 47
Fig. 47. The structure of compound 61–64.
Fig. 48
Fig. 48. The structure of compound 65a–d, 66e–g.
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