Progress in the Synthesis of Boron Dipyrromethene (BODIPY) Fluorescent Dyes

doi:10.6023/cjoc202111001

Abstract

Boron dipyrromethene (BODIPY) dyes are widely used in the fields of life sciences, chemical analysis and optoelectronic materials due to its excellent photophysical properties, favorable biocompatibility, facile synthesis and modification etc. The synthesis and derivative strategies of BODIPY provide the basis for its wide application and have attracted great attention from researchers. In this review, the modification strategies for different reaction positions of BODIPY have been discussed, and Pd-catalyzed cross-coupling reactions and oxidative coupling reactions about BODIPY are discussed individually. Finallly, the development of this field is prospected.

Key words: boron dipyrromethene (BODIPY), fluorescent dyes, synthesis, functional modification

Cite this article

Bin-Kai Liu, Kun-Xu Teng, Li-Ya Niu, Qing-Zheng Yang. Progress in the Synthesis of Boron Dipyrromethene (BODIPY) Fluorescent Dyes[J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1265-1285.

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Fig. & Tab. 27

Figure 1. Number of published literatures on the topic of BODIPY annually (1990~2021, from the database of Web of Science core collection)

Scheme 1. First case of reported BODIPY

Scheme 2. Naming rules of BODIPY

Scheme 3. Synthesis of symmetry BODIPY

Scheme 4. Synthesis of asymmetry BODIPY

Scheme 5. Chlorination of BODIPY’s α positions

Scheme 6. Nucleophilic substitution reactions of BODIPY’s α positions

Scheme 7. GSH probe based on the nucleophilic substitution reaction of BODIPY’s α position

Scheme 8. Knoevenagel condensation reactions of BODIPY’s α positions

Scheme 9. Acylation reactions of BODIPY’s α positions

Scheme 10. Functionalization of formyl group at BODIPY’s α positions

Scheme 11. Radical-mediated reactions of BODIPY’s α positions

Scheme 12. Halogenation of BODIPY’s β positions

Scheme 13. Acylation of BODIPY’s β positions

Scheme 14. Functionalization of formyl groups at BODIPY’s β positions

Scheme 15. Other reactions of BODIPY’s β positions

Scheme 16. Reactions of BODIPY’s γ positions

Scheme 17. Reactions of BODIPY’s meso positions

Scheme 18. Reactions of Biellmann BODIPY’s meso positions

Scheme 19. Synthesis of carbon-boron coordinated BODIPY derivatives

Scheme 20. Synthesis of oxygen-boron coordinated BODIPY derivatives

Scheme 21. Synthesis of chlorine-boron coordinated BODIPY derivatives

Scheme 22. Suzuki-Miyaura reactions of BODIPY

Scheme 23. Sonogashira reactions of BODIPY

Scheme 24. Stille reactions of BODIPY

Scheme 25. Other coupling reactions of BODIPY

Scheme 26. Oxidative coupling reactions of BODIPY

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氟硼二吡咯(BODIPY)荧光染料的合成研究进展