碳硼烷聚集诱导发光化合物的合成研究进展

doi:10.6023/cjoc202412028

摘要/Abstract

作为苯环的三维类似物, 碳硼烷化合物具有独特的三维笼状结构和电子性质, 近年来在调节有机发色团的光物理性质, 构建有机发光化合物方面受到较多关注, 特别是在聚集诱导发光(AIE)化合物的设计合成方面显示了独特的作用. 总结了碳硼烷AIE化合物的结构类型和合成方法, 特别关注了相关合成方法的最新进展. 主要的合成方法包括癸硼烷(衍生物)与相应的炔烃反应构建邻碳硼烷骨架、芳基/烯基/炔基试剂与碳硼烷衍生物反应、AIE化合物与碳硼烷衍生物反应、碳硼烷AIE化合物的转化、碳硼烷B—H键催化活化以及闭式碳硼烷簇合物的脱硼反应等. 在此基础上, 展望了碳硼烷AIE化合物的研究趋势和应用前景.

关键词: 碳硼烷, 聚集诱导发光, 合成, 催化

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

引用此文

闫鹏泽, 高淑莉, 李天瑞, 苗金玲, 蒋绪川, 聂永. 碳硼烷聚集诱导发光化合物的合成研究进展[J]. 有机化学, 2025, 45(8): 2677-2697.

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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图/表 30

图1. 闭式碳硼烷C2B10H12三种异构体的结构(未标注的顶点均为BH)

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

图2. 碳硼烷与AIE基团相连的化合物示例

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

图3. 碳硼烷与碳环相连的AIE化合物示例

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

图4. 碳硼烷与杂环相连的AIE化合物示例

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

图5. 其他类型的碳硼烷AIE化合物示例

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

表1. 碳硼烷AIE化合物的合成方法对比

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

图式1. 化合物1的合成以及类似物1e、1f的化学结构

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

图式2. 化合物9a和23的合成

Scheme 2. Synthesis of compounds 9a and 23

图式3. 化合物15的合成

Scheme 3. Synthesis of compound 15

图式4. 化合物15g、15h的合成

Scheme 4. Synthesis of compounds 15g, 15h

图式5. 化合物15i的合成

Scheme 5. Synthesis of compound 15i

图式6. 化合物25和26的合成

Scheme 6. Synthesis of compounds 25 and 26

图式7. 化合物17的合成

Scheme 7. Synthesis of compound 17

图式8. 化合物9b~9d、15k和27~28的合成

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

图式9. 化合物30的合成

Scheme 9. Synthesis of compound 30

图式10. 化合物2的合成

Scheme 10. Synthesis of compound 2

图式11. 化合物14和35的合成

Scheme 11. Synthesis of compounds 14 and 35

图式12. 化合物36的合成

Scheme 12. Synthesis of compound 36

图式13. 化合物20、37~39的合成

Scheme 13. Synthesis of compounds 20 and 37~39

图式14. 化合物40和41的合成

Scheme 14. Synthesis of compounds 40 and 41

图式15. 化合物42的合成以及43~44的化学结构

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

图式16. 化合物47的合成

Scheme 16. Synthesis of compound 47

图式17. 化合物3~5的合成

Scheme 17. Synthesis of compounds 3~5

图式18. 化合物54a、54b的合成

Scheme 18. Synthesis of compounds 54a, 54b

图式19. 化合物56的转化反应

Scheme 19. Conversions of compound 56

图式20. 笼手性碳硼烷化合物58的合成

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

图式21. 化合物59的合成

Scheme 21. Synthesis of compound 59

图式22. 化合物60和61的合成

Scheme 22. Synthesis of compounds 60 and 61

图式23. 化合物63的合成

Scheme 23. Synthesis of compound 63

图式24. 化合物64的合成

Scheme 24. Synthesis of compound 64

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