碳碳键链接的二维共价有机框架研究进展

doi:10.6023/A23110507

化学学报 ›› 2024, Vol. 82 ›› Issue (1): 75-102.DOI: 10.6023/A23110507 上一篇

综述

碳碳键链接的二维共价有机框架研究进展

魏颖, 王家成, 李玥, 汪涛, 马述威, 解令海^*()

分子系统与有机器件研究中心(CMSOD) 信息材料与纳米技术研究院有机电子与信息显示国家重点实验室(IAM) 南京邮电大学南京 210023

投稿日期:2023-11-21 发布日期:2023-12-19

作者简介:

魏颖, 南京邮电大学材料科学与工程学院副研究员、硕士生导师. 2005至2009年就读于吉林化工学院, 获得学士学位. 2009至2014年就读于东北师范大学化学学院, 获得博士学位. 主要研究方向为有机方法学以及有机/聚合物光电材料的合成及其性能.

解令海, 南京邮电大学信息材料与纳米技术研究院/材料科学与工程学院、博士生导师, 国家百千万人才工程人选, 享受国务院政府特殊津贴. 2000年和2003年分别获得东北师范大学学士学位和汕头大学硕士学位. 2003至2006年就读于复旦大学先进材料研究院, 获得博士学位. 长期从事第四代与智能半导体研发, 柔性电子, 化学智能与智能化学, 人工智能化学家等未来领域的基础研究.

基金资助:
国家自然科学基金(22071112); 国家自然科学基金(22275098); 有机电子与信息显示国家重点实验室资助项目(GDX2022010005)

Research Progress of Carbon-carbon Bond Linked Two-dimensional Covalent-Organic Frameworks

Ying Wei, Jiacheng Wang, Yue Li, Tao Wang, Shuwei Ma, Linghai Xie()

Centre for Molecular Systems and Organic Devices (CMSOD), State Key Laboratory of Organic Electronics and Information Displays & Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications, Nanjing 210023, China

Received:2023-11-21 Published:2023-12-19
Contact: * E-mail: iamlhxie@njupt.edu.cn
Supported by:
National Natural Science Foundation of China(22071112); National Natural Science Foundation of China(22275098); Project of State Key Laboratory of Organic Electronics and Information Displays, Nanjing University of Posts and Telecommunications(GDX2022010005)

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摘要/Abstract

二维共价有机框架(Two-dimensional Covalent-Organic Frameworks, 2D COFs)是指一类由π-共轭构筑单元通过共价键连接形成的具有二维拓扑结构的晶态多孔材料. 由于其独特的周期性多孔结构、高比表面积、优异的稳定性等特点在离子传输、光电材料、催化等领域展现出了巨大的应用潜力. 其中, 碳碳键链接的共价有机框架因兼具优异的稳定性和良好的结晶性, 被认为是最具有前景的二维聚合物材料之一. 近年来, 基于不同的设计原则和合成策略涌现出了许多具有不同结构和优异性能的碳碳键链接共价有机框架. 在这篇综述中, 按照构筑单元的拓扑结构对碳碳键链接共价有机框架进行分类, 并归纳总结了迄今为止C=C和C—C键链接的二维共价有机框架在合成方法、结构创新、性能提升以及实际应用领域的研究进展. 该综述旨在为相关领域的研究人员更好地设计和合成具有多种功能的多孔结晶材料提供参考, 从而促进碳碳键链接共价有机框架材料在光电领域的进一步发展和应用.

关键词: 二维聚合物, 二维共价聚合物, 共价有机框架, 碳碳键链接, 多孔结晶材料

Two-dimensional polymers (2DPs) are a type of planar polymer materials that possess regular porous structures. They fulfill the demand for thin, high-performing, and stable materials in flexible devices, making them highly potential candidates for applications in the field of flexible electronics. As a special class of covalent two-dimensional polymer materials, two-dimensional covalent organic frameworks (COFs) refer to crystalline porous materials with a two-dimensional topology formed by connecting π-conjugated building units through covalent bonds. The unique electronic structure of COFs gives them better electrical properties compared to other two-dimensional polymers. Furthermore, their unique periodic porous structure, high specific surface area, and excellent stability make them highly suitable for various applications such as ion transport, optoelectronic materials, and catalysis. Among these, carbon-carbon bond-linked COFs are regarded as one of the most promising types of two-dimensional polymers due to their excellent stability and good crystallinity. In recent years, many carbon-carbon bonded COFs with different structures and excellent properties have emerged based on different design principles and synthesis strategies. In this review, we summarize and introduce four common synthesis methods for preparing C=C bonded COFs, namely solvent-thermal method, melt-polymerization method, interface polymerization method, and copper template method. Furthermore, we categorize C=C bonded COFs into four classes: [C₂+C₃], [C₂+C₂], [C₃+C₃], and [C₄+C₂], according to the topological structure of the building units. We focus on analyzing the relationship between the composite structure of these COFs and their stability, electrical properties, catalytic performance, and other properties. Additionally, we compile and summarize the research progress of C=C bonded COFs in terms of synthesis methods, structural innovation, performance improvement, and practical applications. This compilation will be beneficial for researchers in the subsequent studies of C=C bonded COFs to select building units based on target structure and performance application and conduct pre-design. Furthermore, this review also includes previously overlooked C—C bonded COFs, providing a more comprehensive reference. In summary, this review aims to provide guidance for researchers in related fields to better design and synthesize multifunctional crystalline porous materials, thereby promoting the further development and application of carbon-carbon bond-linked COFs in various fields.

Key words: two-dimensional polymers, two-dimensional covalent polymers, covalent-organic frameworks, carbon-carbon bond linkage, porous crystalline materials

引用此文

魏颖, 王家成, 李玥, 汪涛, 马述威, 解令海. 碳碳键链接的二维共价有机框架研究进展[J]. 化学学报, 2024, 82(1): 75-102.

Ying Wei, Jiacheng Wang, Yue Li, Tao Wang, Shuwei Ma, Linghai Xie. Research Progress of Carbon-carbon Bond Linked Two-dimensional Covalent-Organic Frameworks[J]. Acta Chimica Sinica, 2024, 82(1): 75-102.

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图/表 58

图1. 共价二维聚合物的制备与表征

Figure 1. Preparation and characterization of two-dimensional covalent polymers

图2. 共价二维聚合物

Figure 2. Two-dimensional covalent polymers

图3. 碳碳键链接COFs近年来的重要进展

Figure 3. Important advances in carbon-carbon bond-linked COFs in recent years

图4. C=C链接COFs的合成反应(a)与制备方法(b)

图5. C=C链接COFs设计的典型拓扑结构图

Figure 5. Typical topology diagram for the design of C=C linked COFs

COF	比表面积/(m²•g^-1)	孔径/nm	孔隙体积/(cm³•g^-1)	孔隙形状
2DPPV	472	1.6	0.37	六边形
sp²c-TFPA-pXD	267	2.7	0.26	六边形
TCPB-DMTA-COF	1069			六边形
TP-COF	232	2	0.19	六边形
COF-701	1366	1.14		六边形
COF1	1008	≈1.1		六边形
g-C₄₀N₃-COF	1235	3.2		六边形
g-C₃₁N₃-COF	864	2.43		六边形
COF-p-NEU1	186	4.93		六边形
COF-p-NEU2	263	4.82		六边形
BTT-Bpy-COF	368	2.85	0.46	六边形
BTH1	644		≈0.6	六边形
BTH2	686		≈0.5	六边形
BTH3	1140		≈0.49	六边形
NDA-TN	1124.3	2.09		六边形
BDA-TN	1070.4	2.51		六边形
ED-TN	863	3.07	0.39	六边形
BD-TN	940	3.58	0.41	六边形
COF-TMT-A	221	1.4		六边形
NKCOF-10	811	1.9		六边形
2D CCP-1	336	0.6/1.3		双孔菱形
2D CCP-2	102	1.2/1.9		双孔菱形
2D CCP-HATN	317	≈0.68/≈1.28		双孔菱形
2D CCP-Th	280	1.0~1.3/1.8~2.0		双孔菱形
2D CCP-BD	410	1.0~1.3/1.8~2.0		双孔菱形
2D-PPQV1	440	0.77/1.38		双孔菱形
2D-PPQV2	100	0.88/1.45		双孔菱形
PTO-COF	957.7	0.67	0.545

表1. [C2+C3]结构C=C链接COFs的孔隙结构

Table 1. The pore structure of C=C linked COFs with [C2+C3] structure

图6. 2DPPV的合成

Figure 6. Synthesis of 2DPPV

图7. sp2-TFPA-pXD的合成

Figure 7. Synthesis of sp2-TFPA-pXD

图8. COF-701的合成

Figure 8. Synthesis of COF-701

图9. 2D-PPQV1和2D-PPQV2的合成

Figure 9. Synthesis of 2D-PPQV1 and 2D-PPQV2

图10. PTO-COF的合成

Figure 10. Synthesis of PTO-COF

图11. TP-COF的合成

Figure 11. Synthesis of TP-COF

图12. COF1, COF2和COF3的合成

Figure 12. Synthesis of COF1, COF2 and COF3

图13. g-C31N3-COF和g-C40N3-COF的合成

Figure 13. Synthesis of g-C31N3-COF and g-C40N3-COF

图14. BTT-BPy-COF的合成与质子化

Figure 14. Synthesis and protonation of BTT-BPy-COF

图15. BTH-1, BTH-2和BTH-3的合成

Figure 15. Synthesis of BTH-1, BTH-2 and BTH-3

图16. NKCOF-10的合成

Figure 16. Synthesis of NKCOF-10

图17. COF-p-NEU1和COF-p-NEU2的合成

Figure 17. Synthesis of COF-p-NEU1 and COF-p-NEU2

图18. sp2c-COF-Ir-ppy2和sp2c-COF-Ru-bpy2的合成

Figure 18. Synthesis of sp2c-COF-Ir-ppy2 and sp2c-COF-Ru-bpy2

图19. NDA-TN-AO的合成

Figure 19. Synthesis of NDA-TN-AO

图20. ED-TN和BD-TN的合成

Figure 20. Synthesis of ED-TN and BD-TN

图21. COF-TMT-A的合成

Figure 21. Synthesis of COF-TMT-A

图22. TCPB-DMTA-COF的合成

Figure 22. Synthesis of TCPB-DMTA-COF

图23. 2D CCP-1和2D CCP-2的合成

Figure 23. Synthesis of 2D CCP-1 and 2D CCP-2

图24. CCP-HATN, 2D CCP-BD和2D CCP-Th的合成

Figure 24. Synthesis of CCP-HATN, 2D CCP-BD and 2D CCP-Th

COF	比表面积/(m²•g^-1)	孔径/nm	孔隙体积/(cm³•g^-1)	孔隙形状
sp²c-COFs-1	613	1.9	0.30	菱形
sp²c-COFs-2	322	2.4	0.14	菱形
sp²c-COFs-3	737	2.7	0.32	菱形
Bpy-sp²c-COF	432	2.4		菱形
CN	364	2.3		菱形
NiCN	258			菱形
Py-BSZ-COF	600	2.4	0.33	菱形
Py-FTP-COF	1780	2.54	0.89	菱形
TFPPy-ICTO-COF	1039	1.8		菱形
TFPPer-ICTO-COF	829	2.1		菱形
F-C_sp²-TT	178	3.9	0.15	菱形
COF_TFBE‑PDAN	936	2.63		菱形
JUC-557	1115	≈1.8	0.637	菱形
CCOF 17		2.4~3.2		菱形
CCOF 18		2.4~3.2		菱形
NKCOF-62	714	0.7	0.59	菱形
sp²c-COF-5	348	1.1/3.7		Kagome
sp²-TPE-COF	25	1.3/2.7	0.22	Kagome
sp²c-COF (kagome)	74.02	1.69/4.34	0.20	Kagome

表2. [C2+C2]结构C=C链接COFs的孔隙结构

Table 2. The pore structure of C=C linked COFs with [C2+C2] structure

图25. Bpy-sp2c-COF和NiCN的合成

Figure 25. Synthesis of Bpy-sp2c-COF and NiCN

图26. Py-BSZ-COF的合成

Figure 26. Synthesis of Py-BSZ-COF

图27. Py-FTP-COF的合成

Figure 27. Synthesis of Py-FTP-COF

图28. sp2c-COF-1~sp2c-COF-3的合成

Figure 28. Synthesis of sp2c-COF-1~sp2c-COF-3

图29. sp2c-gCOF的合成

Figure 29. Synthesis of sp2c-gCOF

图30. TFPPy-ICTO-COF和TFPPer-ICTO-COF的合成

Figure 30. Synthesis of TFPPy-ICTO-COF and TFPPer-ICTO-COF

图31. F-Csp2-TT的合成 F-Csp2-TT的合成

Figure 31. Synthesis of F-Csp2-TT Synthesis of F-Csp2-TT

图32. COFTFBE?PDAN的合成

Figure 32. Synthesis of COFTFBE?PDAN

图33. JUC-557的合成

Figure 33. Synthesis of JUC-557

图34. CCOF 17和CCOF 18的合成

Figure 34. Synthesis of CCOF 17 and CCOF 18

图35. sp2-TPE-COF和sp2c-COF-5的合成

Figure 35. Synthesis of sp2-TPE-COF and sp2c-COF-5

图36. kagome形sp2c-COF的合成

Figure 36. Synthesis of kagome-type sp2c-COFs

图37. 2D-CN-PPV-1的合成

Figure 37. Synthesis of 2D-CN-PPV-1

COF	比表面积/(m²•g^-1)	孔径/nm	孔隙体积/(cm³•g^-1)	孔隙形状
2D-CN-PPV-1	301	1.45		六边形
V-COF-2	627	0.82		六边形
TA-sp²c-COF	496	1.4	0.26	六边形
TM-TPT-COF	810	4.15	0.58	六边形
TTO-COF	390	1.18	0.326	六边形
PT-BN	1149.7	1.45		六边形
PB-AN	967.8	1.44		六边形
TFPT-BTAN	1062	1.44		六边形
TFPT-BTAN-AO	803			六边形
BTE-TBD-COF	490		0.39	六边形
g-C₃₇N₃-COF	1012	1.57		六边形
g-C₃₄N₆-COF	1003	1.45		六边形
g-C₅₄N₆-COF	855	2.38		六边形
g-C₅₂N₆-COF	1000	2.7		六边形

表3. [C3+C3]结构C=C链接COFs的孔隙结构

Table 3. The pore structure of C=C linked COFs with [C3+C3] structure

图38. V-COF-2和g-C33N3-COF的合成

Figure 38. Synthesis of V-COF-2 and g-C33N3-COF

图39. TA-sp2c-COF的合成

Figure 39. Synthesis of TA-sp2c-COF

图40. TM-TPT-COF和TTO-COF的合成

Figure 40. Synthesis of TM-TPT-COF and TTO-COF

图41. BTE-TBD-COF的合成

Figure 41. Synthesis of BTE-TBD-COF

图42. g-C37N3-COF和g-C34N6-COF的合成

Figure 42. Synthesis of g-C37N3-COF and g-C34N6-COF

图43. g-C54N6-COF和g-C52N6-COF的合成

Figure 43. Synthesis of g-C54N6-COF and g-C52N6-COF

图44. PT-BN-AO和TFPT-BTAN-AO的合成

Figure 44. Synthesis of PT-BN-AO and TFPT-BTAN-AO

图45. Por-sp2c-COF的合成

Figure 45. Synthesis of Por-sp2c-COF

COF	比表面积/(m²•g^-1)	孔径/nm	孔隙体积/(cm³•g^-1)	孔隙形状
Por-sp²c-COF	689	1.85		方形

表4. [C2+C4]结构C=C链接COFs的孔隙结构

Table 4. The pore structure of C=C linked COFs with [C2+C4] structure

图46. TA-Por-sp2-COF的合成

Figure 46. Synthesis of TA-Por-sp2-COF

图47. COF-JLU35的合成

Figure 47. Synthesis of COF-JLU35

COF	比表面积/(m²•g^-1)	孔径/nm	孔隙体积/(cm³•g^-1)	孔隙形状
TA-Por-sp²-COF	340.1	1.5		六边形
COF-JLU35	869	2.9	0.48	六边形

表5. 特殊结构C=C链接COFs的孔隙结构

Table 5. The pore structure of C=C linked COFs with special structure

图48. C=C链接COFs的应用

Figure 48. The applications of C=C linked COFs

COF	照射光/nm	催化类型	溶剂	活性/(μmol•g^-1•h^-1)
sp²-COF	>420	光催化析氢	水	1360
g-C₄₀N₃-COF	>420	光催化析氢	水	4120
	>420	光催化析氧	水	2.5
g-C₃₁N₃-COF	>420	光催化析氢	水	542
g-C₃₇N₃-COF	>420	光催化析氢	水	369
g-C₁₈N₃-COF	>420	光催化析氢	水	292
g-C₃₃N₃-COF	>420	光催化析氢	水	74
g-C₅₄N₆-COF	>420	光催化析氢	水	2519
	>420	光催化析氧	水	51
g-C₅₂N₆-COF	>420	光催化析氢	水	1712
	>420	光催化析氧	水	12.5
2DPPV	>420	光催化析氢	水	2330
CCP-Th	>420	光电化学水还原	0.1 mol/L NaSO₄	7.9 μA•cm^-2 0 V
CCP-BD	>420	光电化学水还原	0.1 mol/L NaSO₄
Bpy-sp²-COF	>420	光催化二氧化碳还原	0.1 mol/L NaSO₄	1040 μmol•g^-1•h^-1选择性81%
BTE-TBD-COF	320~780	光催化二氧化碳还原		382 μmol•g^-1•h^-1
Por-sp²-COF	>420	仲胺的光催化氧化	CH₃CN	99%, 0.5 h, r.t.
	623±8	芳基胺的光催化氧化	CH₃CN	90%~98%, 15~30 min, r.t.
Py-BSZ-COF	520	光催化氧化胺偶联	CH₃CN	99%, 12~24 h, r.t.
	520	硫酰胺环化	CH₃CN	56%~91%, 2~48 h, r.t.
TP-COF	420	光催化辅酶再生	磷酸盐缓冲液	90.4%, 10 min, r.t.
TTO-COF	≥420	染料的光催化降解	水	49.9%, 20 min, r.t.
	≥420	芳烃三氟甲基化反应	DMSO	98%, 16 h, r.t.

表6. C=C链接COFs在不同光催化应用中的催化性能

Table 6. Catalytic performance of C=C linked COFs in different photocatalytic applications

COF	比表面积/(m²•g^-1)	孔径/nm	孔隙形状
2DCCOF1		0.3	六边形
2DCCOF2		1.8	方形
Tru-COF	645	1.4	六边形
CCOF 17-R		2.4~3.2	菱形
CCOF 18-R		2.4~3.2	菱形

表7. C—C链接COFs孔隙结构

Table 7. The pore structure of C—C linked COFs

图49. 2DCCOF1和2DCCOF2的合成

Figure 49. Synthesis of 2DCCOF1 and 2DCCOF2

图50. Tru-COF的合成

Figure 50. Synthesis of Tru-COF

图51. CCOF 17-R和CCOF 18-R的合成

Figure 51. Synthesis of CCOF 17-R and CCOF 18-R

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碳碳键链接的二维共价有机框架研究进展

Research Progress of Carbon-carbon Bond Linked Two-dimensional Covalent-Organic Frameworks

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