Progress in the Synthesis of Carborane Compounds with Aggregation-Induced Emission

doi:10.6023/cjoc202412028

Abstract

As three-dimensional analogs of benzene, carboranes have attracted much attention in recent years in modulating the photophysical properties of organic chromophores and constructing organic luminescent compounds due to their unique three-dimensional cage geometries and electronic properties, in particular showing a unique role in the design and synthesis of aggregation-induced emission (AIE) compounds. In this review, the structural types and synthetic methods of carborane AIE compounds are summarized, with a special focus on the new advances in related synthetic methods. The main synthetic methods include constructing the o-carborane skeleton with suitable alkynes and decaborane (derivatives), reactions of aryl/alkenyl/alkynyl reagents with carborane derivatives, reactions of AIE species with carborane derivatives, transformation of carborane AIE compounds, catalytic B—H activation of carborane compounds, and deboronation of the closo-carborane cluster. Based on such progress, the research trends and application prospects of carborane AIE compounds are envisioned.

Key words: carborane, aggregation-induced emission, synthesis, catalysis

Cite this article

Pengze Yan, Shuli Gao, Tianrui Li, Jinling Miao, Xuchuan Jiang, Yong Nie. Progress in the Synthesis of Carborane Compounds with Aggregation-Induced Emission[J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 2677-2697.

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Fig. & Tab. 30

Figure 1. Structures of the three isomers of closo-carborane C2B10H12 (unlabeled vertices are BH)

Figure 2. Examples of compounds with carborane linking to AIE moieties

Figure 3. Examples of AIE compounds with carborane linking to carbon rings

Figure 4. Examples of AIE compounds with carborane linking to heterocycles

Figure 5. Example of other type of carborane AIE compound

Synthetic methods	Advantages	Disadvantages
Reactions of aryl alkynes with decaboran derivatives	Broad substrate scope, one step reaction	Toxic borane material, relatively low yields
Reactions of aryl/alkenyl/alkynyl reagents with carborane derivatives	Broad substrate scope, relatively high- yielding	Complex procedure, limited application, sometimes requires metal catalysis
Reactions of AIE species with carborane derivatives	Broad substrate scope, versatile functional group incorporation	Limited precursor availability
Transformation of carborane AIE compounds	Preserves the compound’s skeleton, relatively high-yielding	Pre-synthesis of AIE compounds, limited application
Catalytic B—H activation of carborane compounds	Broad substrate scope, relatively high- yielding	Requires directing group/auxiliary agent and noble metal catalysts
Deboronation of the closo-carborane cluster	Broad substrate scope, simple procedure	Limited application

Table 1. Comparison of the synthetic methods of carborane AIE compounds

Scheme 1. Synthesis of compound 1 and chemical structures of 1e, 1f

Scheme 2. Synthesis of compounds 9a and 23

Scheme 3. Synthesis of compound 15

Scheme 4. Synthesis of compounds 15g, 15h

Scheme 5. Synthesis of compound 15i

Scheme 6. Synthesis of compounds 25 and 26

Scheme 7. Synthesis of compound 17

Scheme 8. Synthesis of compounds 9b~9d, 15k and 27~28

Scheme 9. Synthesis of compound 30

Scheme 10. Synthesis of compound 2

Scheme 11. Synthesis of compounds 14 and 35

Scheme 12. Synthesis of compound 36

Scheme 13. Synthesis of compounds 20 and 37~39

Scheme 14. Synthesis of compounds 40 and 41

Scheme 15. Synthesis of compound 42 and chemical structures of 43~44

Scheme 16. Synthesis of compound 47

Scheme 17. Synthesis of compounds 3~5

Scheme 18. Synthesis of compounds 54a, 54b

Scheme 19. Conversions of compound 56

Scheme 20. Synthesis of chiral-at-cage carborane compound 58

Scheme 21. Synthesis of compound 59

Scheme 22. Synthesis of compounds 60 and 61

Scheme 23. Synthesis of compound 63

Scheme 24. Synthesis of compound 64

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