含咔唑结构的小分子及聚合物催化二氧化碳转化研究进展

doi:10.6023/cjoc202311016

摘要/Abstract

咔唑具有刚性平面结构和共轭π电子特征, 表现出优异的电子传输性质. 咔唑的N原子和芳环上容易进行化学修饰, 以咔唑作为骨架或连接单元, 人们方便地开发出结构多样的咔唑基配体和聚合物, 并在催化和功能材料等研究领域中得到了广泛的应用. 二氧化碳催化转化制备燃料和化学品, 可以为实现双碳目标提供重要的技术支撑. 综述了近年来咔唑基配体、咔唑基金属配合物及含咔唑结构的多相材料在催化CO₂相关反应方面的研究进展. 通过介绍催化剂制备方法, 归纳总结均相催化以及多相催化反应等内容, 将为深入理解咔唑单元在催化中的重要作用, 提升咔唑基材料的催化效率提供重要的参考信息.

关键词: 咔唑结构, 二氧化碳, 均相催化, 多相催化, 电子传递

Carbazole moiety exhibits excellent electron transfer ability due to its rigid planar structure and large conjugate system. The N atom and aromatic ring of carbazole can be easily modified, and carbazole-based ligands and polymers have attracted significant amounts of interests in the fields of catalysis and material sciences. Important progress has been achieved in both homogeneous and heterogeneous catalysis promoted by catalysts containing carbazole as the backbone or linker. The catalytic conversion of carbon dioxide can provide an important technology support for realization of carbon neutrality goals. In this paper, the recent progresses on the use of carbazole-based ligands, carbazole-based complexes or carbazole-based heterogeneous materials in catalytic transformation of CO₂ are reviewed, including the methods of catalyst preparation, the different types of reactions in homogeneous and heterogeneous catalysis. This review will provide systematic information for further understanding the important role of carbazole units in catalysis and designing more efficient carbazole-based materials.

Key words: carbazole structure, carbon dioxide, homogeneous catalysis, heterogeneous catalysis, electron transfer

引用此文

姜晓琳, 王超洋, 武利园, 李跃辉. 含咔唑结构的小分子及聚合物催化二氧化碳转化研究进展[J]. 有机化学, 2024, 44(5): 1423-1444.

Xiaolin Jiang, Chaoyang Wang, Liyuan Wu, Yuehui Li. Advances in Catalytic Conversion of CO₂ with Carbazole-Based Molecules and Polymers[J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1423-1444.

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图/表 33

图1. 部分CNC型咔唑pincer配体及配合物

Figure 1. Some CNC carbazole pincer ligands and metal complexes

图2. CNC型咔唑pincer配体在聚合和环加成反应中的应用

Figure 2. Application of CNC carbazole pincer ligands in poly- merization and cycloaddition reactions

图3. CNC型咔唑pincer配体在环加成反应中的应用

Figure 3. Application of CNC carbazole pincer ligands in cycloaddition reactions

图4. CNC型咔唑pincer配体在催化环氧化合物脱氧反应中的应用

Figure 4. Application of CNC carbazole pincer ligands in catalytic deoxygenation of epoxides

图5. 部分PNP型咔唑pincer配体及金属配合物

Figure 5. Some PNP carbazole pincer ligands and metal complexes

图6. PNP咔唑-T型铁配合物与CO2的反应活性

Figure 6. Reactivity of PNP carbazole pincer T-typed Iron(I) complexes with CO2

图7. 部分NNN型咔唑pincer配体及金属配合物

Figure 7. Some NNN carbazole pincer ligands and metal complexes

图8. 咔唑膦配体在CO2还原酰胺化、甲基化反应中的应用

Figure 8. Application of carbazole-phosphine ligands in CO2 reduction formylation and methylation reactions

图9. 咔唑氮-膦基配体在CO2和芳基碘硫酯化反应中的应用

Figure 9. Application of N-P carbazole ligands in the thiocarbonylation of aryl iodides with CO2

图10. 咔唑膦配体的官能团化修饰及在CO2参与反应中的应用

Figure 10. Functionalized carbazole-phosphine ligands and applications in CO2 involved reactions

图11. 咔唑膦配体在端炔羰基化反应中的应用

Figure 11. Application of carbazole-phosphine ligands in the carbonylation of terminal alkyne

图12. 咔唑膦配体在端烯羰基化反应中的应用

Figure 12. Application of carbazole-phosphine ligands in the carbonylation of alkene

图13. N-杂环取代修饰的1,10-邻菲罗啉配体-Re金属配合物

Figure 13. Rhenium complexes with 1,10-phenanthroline ligand bearing N-heterocyclic substituents

图14. 新型钳形双NHC咔唑镍配合物催化CO2还原

Figure 14. Application of novel double NHC carbazole nickel complex in CO2 reduction

图15. 部分二氰基苯骨架光敏剂的结构

Figure 15. Some structure of photosensitizer with dicyanobenzene backbone

图16. 4CzIPN催化苄位C—H键羧基化的反应机理

Figure 16. Mechanism of the carboxylation of C—H bond at the benzyl position catalyzed by 4CzIPN

图17. 4CzIPN作光敏剂实现CO2参与的光催化反应

Figure 17. Photocatalytic reaction involving CO2 using 4CzIPN as a photosensitizer

图18. 4CzIPN-三联吡啶-Fe体系在CO2光还原中的应用

Figure 18. Application of 4CzIPN-terpyridine-Fe system in CO2 photoreduction

图19. 4CzIPN-三联吡啶-金属体系在CO2的光还原中的应用

Figure 19. Application of 4CzIPN-terpyridine-metal system in CO2 photoreduction

图20. 不含金属的CO2光还原体系

Figure 20. CO2 photoreduction system without metal catalysts

图21. 吡啶基多孔聚咔唑金属铼材料在CO2光还原中的应用

Figure 21. Application of Re-metalated polypyridine-based porous polycarbazoles in CO2 photoreduction

图22. 多孔聚咔唑-金属复合物在CO2光还原中的应用

Figure 22. Application of metalated porous polycarbazole complexes in CO2 photoreduction

图23. 咔唑聚合物-金属配合物在CO2光还原中的应用

Figure 23. Application of carbazole-based polymer metal complexes in CO2 photoreduction

图24. 咔唑基复合金属材料在CO2光还原中的应用

Figure 24. Application of carbazole-based composite metal materials in CO2 photoreduction

图25. 咔唑-三嗪共价有机框架材料在CO2光还原中的应用

Figure 25. Application of carbazole-triazine covalent organic framework in CO2 photoreduction

图26. 吡啶连接的咔唑基有机聚合材料在CO2光还原中的应用

Figure 26. Application of carbazolyl-based pyridine conjugated organic polymers in CO2 photoreduction

图27. 光敏剂和咔唑共聚的多孔有机聚合物实现CO2光还原

Figure 27. Photoreduction of CO2 with porous organic polymer achieved by copolymerization of photosensitizer and carbazole

图28. 咔唑树枝状大分子修饰Au电极实现CO2电还原

Figure 28. Carbazole dendrimer modified Au electrodes for CO2 electroreduction

图29. 咔唑树枝状大分子修饰Au电极实现CO2电还原

Figure 29. Carbazole dendrimer modified Au electrodes for CO2 electroreduction

图30. 金属铜氧化物嵌入咔唑聚合物实现CO2电羧基化反应

Figure 30. Electrocarboxylation reaction of CO2 achieved Cu-embedded carbazole-derived porous organic polymer nanohybrid

图31. 钯纳米粒子负载的咔唑基超交联聚合物催化CO2还原酰胺化反应

Figure 31. Reductive formylation of CO2 with Pd nanoparticles decorated on hypercrosslinked polymer bearing carbazole

图32. 银纳米粒子负载的咔唑基超交联微孔聚合物催化CO2反应

Figure 32. Reaction of CO2 with Ag nanoparticles decorated on hypercrosslinked porous polymer bearing carbazole

图33. 咔唑共价三嗪框架材料在CO2环加成反应中的应用

Figure 33. Application of carbazole-based covalent triazine frameworks in CO2 cycloaddition reactions

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