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

doi:10.6023/A23110507

Acta Chimica Sinica ›› 2024, Vol. 82 ›› Issue (1): 75-102.DOI: 10.6023/A23110507 Previous Articles

Review

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)

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

Cite this article

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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References 122

[1]	Wang, P.; Hu, M.; Wang, H.; Chen, Z.; Feng, Y.; Wang, J.; Ling, W.; Huang, Y. Adv. Sci. 2020, 7, 2001116. doi: 10.1002/advs.v7.20
[2]	Nathan, A.; Ahnood, A.; Cole, M. T.; Lee, S.; Suzuki, Y.; Hiralal, P.; Bonaccorso, F.; Hasan, T.; Garcia-Gancedo, L.; Dyadyusha, A. Proc. IEEE 2012, 100, 1486. doi: 10.1109/JPROC.2012.2190168
[3]	Stoppa, M.; Chiolerio, A. Sensors 2014, 14, 11957. doi: 10.3390/s140711957
[4]	Aftab, S.; Hegazy, H. H.; Kabir, F. Adv. Mater. Technol. 2023, 2201897.
[5]	Hoang, A. T.; Hu, L.; Katiyar, A. K.; Ahn, J.-H. Matter 2022, 5, 4116. doi: 10.1016/j.matt.2022.10.016
[6]	Novoselov, K. S.; Geim, A. K.; Morozov, S. V.; Jiang, D.; Zhang, Y.; Dubonos, S. V.; Grigorieva, I. V.; Firsov, A. A. Science 2004, 306, 666. doi: 10.1126/science.1102896 pmid: 15499015
[7]	Butler, S. Z.; Hollen, S. M.; Cao, L.; Cui, Y.; Gupta, J. A.; Gutiérrez, H. R.; Heinz, T. F.; Hong, S. S.; Huang, J.; Ismach, A. F. ACS Nano 2013, 7, 2898. doi: 10.1021/nn400280c
[8]	Chang, C.; Chen, W.; Chen, Y.; Chen, Y.-H.; Chen, Y.; Ding, F.; Fan, C.-H.; Fan, H.-J.; Fan, Z.-X.; Gong, C.; Gong, Y.-J.; He, Q.-Y.; Hong, X.; Hu, S.; Hu, W.-D.; Huang, W.; Huang, Y.; Ji, W.; Li, D.-H.; Li, L.-J.; Li, Q.; Lin, L.; Ling, C.-Y.; Liu, M-H.; Liu, N.; Liu, Z.; Kian, P. L.; Ma, J.-M.; Miao, F.; Peng, J.-M.; Ma, H-L.; Shao, M-F.; Song, L.; Su, S.; Sun, S.; Tan, C-L.; Tang, Z.-Y.; Wang, D-S.; Wang, H.; Wang, J.-L.; Wang, X.; Wang, X.-R.; Wee, A. T. S.; Wei, Z.-M.; Wu, Y.-E.; Wu, Z.-S.; Xiong, J.; Xiong, Q.-H.; Xu, W.-G.; Yin, P.; Zeng, H.-B.; Zeng, Z.-Y.; Zhai, T.-Y.; Zhang, H.; Zhang, H.; Zhang, Q.-C.; Zhang, T.-R.; Zhang, X.; Zhao, L.-D.; Zhao, M.-T.; Zhao, W.-J.; Zhao, Y.-X.; Zhou, K.-G.; Zhou, X.; Zhou, Y.; Zhu, H.-W.; Zhang, H.; Liu, Z.-F. Acta Phys.-Chim. Sin. 2021, 37, 2108017.
[9]	Sakamoto, J.; van Heijst, J.; Lukin, O.; Schlüter, A. D. Angew. Chem. Int. Ed. 2009, 48, 1030. doi: 10.1002/anie.200801863 pmid: 19130514
[10]	Servalli, M.; Schlüter, A. D. Annu. Rev. Mater. Res. 2017, 47, 361. doi: 10.1146/matsci.2017.47.issue-1
[11]	Li, S.-Z.; Huang, X.; Zhang, H. Acta Chim. Sinica 2015, 73, 913. doi: 10.6023/A15030221
[12]	Thomas, S.; Li, H.; Zhong, C.; Matsumoto, M.; Dichtel, W. R.; Bredas, J.-L. Chem. Mater. 2019, 31, 3051. doi: 10.1021/acs.chemmater.8b04986
[13]	Chen, J.-C.; Zhang, M.-X.; Wang, S.-A. Acta Chim. Sinica 2023, 81, 146. (in Chinese) doi: 10.6023/A22100442
	(陈俊畅, 张明星, 王殳凹, 化学学报, 2023, 81, 146.) doi: 10.6023/A22100442
[14]	Stupp, S.; Son, S.; Lin, H.-C.; Li, L. Science 1993, 259, 59. pmid: 17757473
[15]	Berlanga, I.; Ruiz-González, M. L.; González-Calbet, J. M.; Fierro, J. L. G.; Mas-Ballesté, R.; Zamora, F. Small 2011, 7, 1207. doi: 10.1002/smll.201002264 pmid: 21491587
[16]	Kissel, P.; Erni, R.; Schweizer, W. B.; Rossell, M. D.; King, B. T.; Bauer, T.; Götzinger, S.; Schlüter, A. D.; Sakamoto, J. Nat. Chem. 2012, 4, 287. doi: 10.1038/nchem.1265
[17]	Grill, L.; Dyer, M.; Lafferentz, L.; Persson, M.; Peters, M. V.; Hecht, S. Nat. Nanotechnol. 2007, 2, 687. doi: 10.1038/nnano.2007.346
[18]	Colson, J. W.; Woll, A. R.; Mukherjee, A.; Levendorf, M. P.; Spitler, E. L.; Shields, V. B.; Spencer, M. G.; Park, J.; Dichtel, W. R. Science 2011, 332, 228. doi: 10.1126/science.1202747 pmid: 21474758
[19]	Zhou, T.-Y.; Lin, F.; Li, Z.-T.; Zhao, X. Macromolecules 2013, 46, 7745. doi: 10.1021/ma401570g
[20]	Evans, A. M.; Strauss, M. J.; Corcos, A. R.; Hirani, Z.; Ji, W.; Hamachi, L. S.; Aguilar-Enriquez, X.; Chavez, A. D.; Smith, B. J.; Dichtel, W. R. Chem. Rev. 2021, 122, 442. doi: 10.1021/acs.chemrev.0c01184
[21]	Feng, X.; Ding, X.; Jiang, D. Chem. Soc. Rev. 2012, 41, 6010. doi: 10.1039/c2cs35157a
[22]	Li, L.-L.; Liu, S.; Zhang, Q.; Hu, N.-T.; Wei, L.-M.; Yang, Z.; Wei, H. Acta Physico-Chim. Sinica 2017, 33, 1960. (in Chinese)
	(李路路, 刘帅, 章琴, 胡南滔, 魏良明, 杨志, 魏浩, 物理化学学报, 2017, 33, 1960.)
[23]	Ding, S.-Y.; Wang, W. Chem. Soc. Rev. 2013, 42, 548. doi: 10.1039/C2CS35072F
[24]	Cote, A. P.; Benin, A. I.; Ockwig, N. W.; O'Keeffe, M.; Matzger, A. J.; Yaghi, O. M. Science 2005, 310, 1166. doi: 10.1126/science.1120411
[25]	Huang, N.; Wang, P.; Jiang, D. Nat. Rev. Mater. 2016, 1, 16068. doi: 10.1038/natrevmats.2016.68
[26]	Yuan, C.; Fu, S.; Yang, K.; Hou, B.; Liu, Y.; Jiang, J.; Cui, Y. J. Am. Chem. Soc. 2020, 143, 369. doi: 10.1021/jacs.0c11050
[27]	Yu, G.; Wang, C. Chinese J. Org. Chem. 2020, 40, 1437. (in Chinese) doi: 10.6023/cjoc202003018
	(于歌, 汪成, 有机化学, 2020, 40, 1437). doi: 10.6023/cjoc202003018
[28]	Xu, S.; Li, Y.; Biswal, B. P.; Addicoat, M. A.; Paasch, S.; Imbrasas, P.; Park, S.; Shi, H.; Brunner, E.; Richter, M.; Lenk, S.; Reineke, S.; Feng, X.-L. Chem. Mater. 2020, 32, 7985. doi: 10.1021/acs.chemmater.0c02910
[29]	Zhuang, X.; Zhao, W.; Zhang, F.; Cao, Y.; Liu, F.; Bi, S.; Feng, X. Polym. Chem. 2016, 7, 4176. doi: 10.1039/C6PY00561F
[30]	Jin, E.; Li, J.; Geng, K.; Jiang, Q.; Xu, H.; Xu, Q.; Jiang, D. Nat. Commun. 2018, 9, 4143. doi: 10.1038/s41467-018-06719-8
[31]	Zhao, Y.; Liu, H.; Wu, C.; Zhang, Z.; Pan, Q.; Hu, F.; Wang, R.; Li, P.; Huang, X.; Li, Z. Angew. Chem. Int. Ed. 2019, 58, 5376. doi: 10.1002/anie.v58.16
[32]	Xu, S.; Wang, G.; Biswal, B. P.; Addicoat, M.; Paasch, S.; Sheng, W.; Zhuang, X.; Brunner, E.; Heine, T.; Berger, R.; Feng, X.-L. Angew. Chem. Int. Ed. 2019, 58, 849. doi: 10.1002/anie.v58.3
[33]	Cheng, Y.-J.; Yang, S.-H.; Hsu, C.-S. Chem. Rev. 2009, 109, 5868. doi: 10.1021/cr900182s
[34]	Pastoetter, D. L.; Xu, S.; Borrelli, M.; Addicoat, M.; Biswal, B. P.; Paasch, S.; Dianat, A.; Thomas, H.; Berger, R.; Reineke, S.; Brunner, E.; Cuniberti, G.; Richter, M.; Feng, X.-L. Angew. Chem. Int. Ed. 2020, 59, 23620. doi: 10.1002/anie.202010398 pmid: 32959467
[35]	Jin, E.; Geng, K.; Lee, K. H.; Jiang, W.; Li, J.; Jiang, Q.; Irle, S.; Jiang, D. Angew. Chem. Int. Ed. 2020, 59, 12162. doi: 10.1002/anie.v59.29
[36]	Wang, Z.; Yang, Y.; Zhao, Z.; Zhang, P.; Zhang, Y.; Liu, J.; Ma, S.; Cheng, P.; Chen, Y.; Zhang, Z. Nat. Commun. 2021, 12, 1982. doi: 10.1038/s41467-021-22288-9
[37]	Wang, Z.; Zhang, Y.; Lin, E.; Geng, S.; Wang, M.; Liu, J.; Chen, Y.; Cheng, P.; Zhang, Z. J. Am. Chem. Soc. 2023, 145, 21483. doi: 10.1021/jacs.3c07224
[38]	Wu, D.; Che, Q.; He, H.; El-Khouly, M. E.; Huang, S.; Zhuang, X.; Zhang, B.; Chen, Y. ACS Mater. Lett. 2023, 5, 874.
[39]	Yan, H.; Kou, Z.; Li, S.; Zhang, T. Small 2023, 2207972.
[40]	Shanavaz, H.; Kannanugu, N.; Kasai, D.; Kumar, K. Y.; Raghu, M.; Prashanth, M.; Khan, M. A.; Jeon, B.-H.; Linul, E. J. Energy Storage 2023, 71, 108006. doi: 10.1016/j.est.2023.108006
[41]	He, T.; Geng, K.; Jiang, D. Trends Chem. 2021, 3, 431. doi: 10.1016/j.trechm.2021.03.008
[42]	Yu, G.; Liu, Y.; Yang, X.; Li, Y.; Li, Y.; Zhang, Y.; He, C. Sep. Purif. Technol. 2023, 312, 123401. doi: 10.1016/j.seppur.2023.123401
[43]	Cui, Y.; Fang, Q.; Lei, H.; Xue, G.; Yu, W. Chem. Phys. Lett. 2003, 377, 507. doi: 10.1016/S0009-2614(03)01207-7
[44]	Lenz, R. W.; Handlovits, C. E. J. Org. Chem. 1960, 25, 813. doi: 10.1021/jo01075a038
[45]	Lyu, H.; Diercks, C. S.; Zhu, C.; Yaghi, O. M. J. Am. Chem. Soc. 2019, 141, 6848. doi: 10.1021/jacs.9b02848
[46]	Bi, S.; Yang, C.; Zhang, W.; Xu, J.; Liu, L.; Wu, D.; Wang, X.; Han, Y.; Liang, Q.; Zhang, F. Nat. Commun. 2019, 10, 2467. doi: 10.1038/s41467-019-10504-6
[47]	Xu, J.; He, Y.; Bi, S.; Wang, M.; Yang, P.; Wu, D.; Wang, J.; Zhang, F. Angew. Chem. Int. Ed. 2019, 58, 13753. doi: 10.1002/anie.v58.39
[48]	Ando, K. J. Org. Chem. 1999, 64, 6815. doi: 10.1021/jo9909150
[49]	Kurti, L.; Czakó, B., Strategic applications of named reactions in organic synthesis, Elsevier, Burlington, 2005, pp. 502-508.
[50]	Yang, Y.; Zhao, W.; Niu, H.; Cai, Y. ACS Appl. Mater. Inter. 2021, 13, 42035. doi: 10.1021/acsami.1c11775
[51]	Zhao, Y.; Liu, H.; Wu, C.; Zhang, Z.; Pan, Q.; Hu, F.; Wang, R.; Li, P.; Huang, X.; Li, Z. Angew. Chem. Int. Ed. 2019, 58, 5376. doi: 10.1002/anie.v58.16
[52]	Duan, J.; Chen, S.; Jaroniec, M.; Qiao, S. Z. ACS Nano 2015, 9, 931. doi: 10.1021/nn506701x
[53]	Liu, J.; Wang, H.; Antonietti, M. Chem. Soc. Rev. 2016, 45, 2308. doi: 10.1039/C5CS00767D
[54]	Wang, X.; Maeda, K.; Thomas, A.; Takanabe, K.; Xin, G.; Carlsson, J. M.; Domen, K.; Antonietti, M. Nat. Mater. 2009, 8, 76. doi: 10.1038/nmat2317
[55]	Jadhav, T.; Fang, Y.; Patterson, W.; Liu, C. H.; Hamzehpoor, E.; Perepichka, D. F. Angew. Chem. Int. Ed. 2019, 58, 13753. doi: 10.1002/anie.v58.39
[56]	Acharjya, A.; Pachfule, P.; Roeser, J.; Schmitt, F. J.; Thomas, A. Angew. Chem. Int. Ed. 2019, 58, 14865. doi: 10.1002/anie.201905886 pmid: 31340082
[57]	Wei, S.; Zhang, F.; Zhang, W.; Qiang, P.; Yu, K.; Fu, X.; Wu, D.; Bi, S.; Zhang, F. J. Am. Chem. Soc. 2019, 141, 14272. doi: 10.1021/jacs.9b06219
[58]	Shi, T.; Wang, H.; Li, L.; Zhao, Z.; Wang, C.; Zhang, X.; Xie, Y. Matter 2022, 5, 1004. doi: 10.1016/j.matt.2022.01.003
[59]	Friend, R. H.; Gymer, R.; Holmes, A.; Burroughes, J.; Marks, R.; Taliani, C.; Bradley, D.; Santos, D. D.; Bredas, J.-L.; Lögdlund, M.; Salaneck, W. R. Nature 1999, 397, 121. doi: 10.1038/16393
[60]	Ng, S. C.; Lu, H. F.; Chan, H. S.; Fujii, A.; Laga, T.; Yoshino, K. Adv. Mater. 2000, 12, 1122. doi: 10.1002/(ISSN)1521-4095
[61]	Dai, L.; Dong, A.; Meng, X.; Liu, H.; Li, Y.; Li, P.; Wang, B. Angew. Chem. Int. Ed. 2023, 62, e202300224. doi: 10.1002/anie.v62.15
[62]	Wang, Y.; Hao, W.; Liu, H.; Chen, R.; Pan, Q.; Li, Z.; Zhao, Y. Nat. Commun. 2022, 13, 100. doi: 10.1038/s41467-021-27573-1
[63]	Sen, S.; Al-Sayah, M. H.; Mohammed, M. S.; Abu-Abdoun, I. I.; El-Kadri, O. M. J. Mater. Sci. 2020, 55, 10896. doi: 10.1007/s10853-020-04741-0
[64]	Sun, S. N.; Dong, L. Z.; Li, J. R.; Shi, J. W.; Liu, J.; Wang, Y. R.; Huang, Q.; Lan, Y. Q. Angew. Chem. Int. Ed. 2022, 61, e202207282. doi: 10.1002/anie.v61.34
[65]	Yang, S.; Sa, R.; Zhong, H.; Lv, H.; Yuan, D.; Wang, R. Adv. Funct. Mater. 2022, 32, 2110694. doi: 10.1002/adfm.v32.17
[66]	Xu, Y.; Wu, C.; Chu, N.; Xing, Y.; Yang, J.; Yin, L.; Chen, X. Sep. Purif. Technol. 2023, 307, 1383.
[67]	Sun, B.; Wang, X.; Ye, Z.; Zhang, J.; Chen, X.; Zhou, N.; Zhang, M.; Yao, C.; Wu, F.; Shen, J. Adv. Sci. 2023, 10, e2207507.
[68]	Cui, W. R.; Li, F. F.; Xu, R. H.; Zhang, C. R.; Chen, X. R.; Yan, R. H.; Liang, R. P.; Qiu, J. D. Angew. Chem. Int. Ed. 2020, 59, 17684. doi: 10.1002/anie.v59.40
[69]	Zhang, C.-R.; Cui, W.-R.; Xu, R.-H.; Chen, X.-R.; Jiang, W.; Wu, Y.-D.; Yan, R.-H.; Liang, R.-P.; Qiu, J.-D. CCS Chem. 2021, 3, 168. doi: 10.31635/ccschem.020.202000618
[70]	Lei, T.; Mi, Y.; Wei, Z.; Li, S.; Pang, S. Dalton Trans. 2023, 52, 1761. doi: 10.1039/D2DT03743B
[71]	Wang, H.; Wang, F.; Wu, T.; Liu, Y. Anal. Chem. 2021, 93, 15794. doi: 10.1021/acs.analchem.1c04130
[72]	Cui, L.; Zhu, C.-Y.; Hu, J.; Meng, X.-M.; Jiang, M.; Gao, W.; Wang, X.; Zhang, C.-Y. Sens. Actuators B Chem. 2023, 374, 132779. doi: 10.1016/j.snb.2022.132779
[73]	Zhang, X.; Ren, C.; Hu, F.; Gao, Y.; Wang, Z.; Li, H.; Liu, J.; Liu, B.; Yang, C. Anal. Chem. 2020, 92, 5185. doi: 10.1021/acs.analchem.9b05704 pmid: 32207924
[74]	Caruso, U.; Panunzi, B.; Diana, R.; Concilio, S.; Sessa, L.; Shikler, R.; Nabha, S.; Tuzi, A.; Piotto, S. Molecules 2018, 231947. doi: 10.3390/molecules23081947
[75]	Xu, F.; Jin, S.; Zhong, H.; Wu, D.; Yang, X.; Chen, X.; Wei, H.; Fu, R.; Jiang, D. Sci. Rep. 2015, 5, 8225. doi: 10.1038/srep08225
[76]	Xu, S.; Sun, H.; Addicoat, M.; Biswal, B. P.; He, F.; Park, S.; Paasch, S.; Zhang, T.; Sheng, W.; Brunner, E.; Hou, Y.; Richter, M.; Feng, X.-L. Adv. Mater. 2021, 33, 2006274. doi: 10.1002/adma.v33.1
[77]	Fu, Z.; Wang, X.; Gardner, A. M.; Wang, X.; Chong, S. Y.; Neri, G.; Cowan, A. J.; Liu, L.; Li, X.; Vogel, A.; Clowes, R.; Bilton, M.; Chen, L.; Sprick, R. S.; Cooper, A. I. Chem. Sci. 2020, 11, 543. doi: 10.1039/C9SC03800K
[78]	Fan, Y.; Kang, D. W.; Labalme, S.; Li, J.; Lin, W. Angew. Chem. Int. Ed. 2023, 62, e202218908. doi: 10.1002/anie.v62.11
[79]	Luo, J.; Lu, J.; Zhang, J. J. Mater. Chem. A 2018, 6, 15154. doi: 10.1039/C8TA05329D
[80]	Ou, W.; Zhang, G.; Wu, J.; Su, C. ACS Catal. 2019, 9, 5178. doi: 10.1021/acscatal.9b00693
[81]	Li, S.; Li, L.; Li, Y.; Dai, L.; Liu, C.; Liu, Y.; Li, J.; Lv, J.; Li, P.; Wang, B. ACS Catal. 2020, 10, 8717. doi: 10.1021/acscatal.0c01242
[82]	Chen, W.; Wang, L.; Mo, D.; He, F.; Wen, Z.; Wu, X.; Xu, H.; Chen, L. Angew. Chem. Int. Ed. 2020, 59, 16902. doi: 10.1002/anie.v59.39
[83]	Wang, G.-B.; Xie, K.-H.; Kan, J.-L.; Xu, H.-P.; Zhao, F.; Wang, Y.-J.; Geng, Y.; Dong, Y.-B. Chem. Commun. 2023, 59, 1493. doi: 10.1039/D2CC06228C
[84]	Ma, T.; Li, J.; Niu, J.; Zhang, L.; Etman, A. S.; Lin, C.; Shi, D.; Chen, P.; Li, L.-H.; Du, X. J. Am. Chem. Soc. 2018, 140, 6763. doi: 10.1021/jacs.8b03169
[85]	Wan, S.; Guo, J.; Kim, J.; Ihee, H.; Jiang, D. Angew. Chem. Int. Ed. 2008, 47, 8862.
[86]	Wan, S.; Guo, J.; Kim, J.; Ihee, H.; Jiang, D. Angew. Chem. Int. Ed. 2009, 48, 5439. doi: 10.1002/anie.v48:30
[87]	Jin, E.; Asada, M.; Xu, Q.; Dalapati, S.; Addicoat, M. A.; Brady, M. A.; Xu, H.; Nakamura, T.; Heine, T.; Chen, Q. Science 2017, 357, 673. doi: 10.1126/science.aan0202
[88]	Cui, W.-R.; Zhang, C.-R.; Jiang, W.; Li, F.-F.; Liang, R.-P.; Liu, J.; Qiu, J.-D. Nat. Commun. 2020, 11, 436. doi: 10.1038/s41467-020-14289-x
[89]	Blondeau, P.; Segura, M.; Pérez-Fernández, R.; de Mendoza, J. Chem. Soc. Rev. 2007, 36, 198. pmid: 17264923
[90]	Bai, C.; Qiang, L.; Zhang, B.; Gao, K.; Zhang, J. Friction 2022, 10, 866. doi: 10.1007/s40544-021-0498-0
[91]	Das, S.; Hazarika, G.; Manna, D. Chem. Eur. J. 2023, 29, e202203595. doi: 10.1002/chem.v29.15
[92]	Wang, H.-G.; Yuan, S.; Si, Z.; Zhang, X.-B. Energy Environ. Sci. 2015, 8, 3160. doi: 10.1039/C5EE02589C
[93]	Xu, X.; Zhang, S.; Xu, K.; Chen, H.; Fan, X.; Huang, N. J. Am. Chem. Soc. 2023, 145, 1022. doi: 10.1021/jacs.2c10509
[94]	Zhang, Y.; Liu, H.; Sun, B. J. Hazard. Mater. 2023, 448, 130866. doi: 10.1016/j.jhazmat.2023.130866
[95]	Luo, J.; Xie, Z.; Lam, J. W.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D. Chem. Commun. 2001, 1740.
[96]	Dalapati, S.; Jin, E.; Addicoat, M.; Heine, T.; Jiang, D. J. Am. Chem. Soc. 2016, 138, 5797. doi: 10.1021/jacs.6b02700 pmid: 27108740
[97]	Ding, H.; Li, J.; Xie, G.; Lin, G.; Chen, R.; Peng, Z.; Yang, C.; Wang, B.; Sun, J.; Wang, C. Nat. Commun. 2018, 9, 5234. doi: 10.1038/s41467-018-07670-4
[98]	You, J.; Yuan, F.; Cheng, S.; Kong, Q.; Jiang, Y.; Luo, X.; Xian, Y.; Zhang, C. Chem. Mater. 2022, 34, 7078. doi: 10.1021/acs.chemmater.2c01726
[99]	Dong, J.; Li, X.; Peh, S. B.; Yuan, Y. D.; Wang, Y.; Ji, D.; Peng, S.; Liu, G.; Ying, S.; Yuan, D. Chem. Mater. 2018, 31, 146. doi: 10.1021/acs.chemmater.8b03685
[100]	Guan, X.; Li, H.; Ma, Y.; Xue, M.; Fang, Q.; Yan, Y.; Valtchev, V.; Qiu, S. Nat. Chem. 2019, 11, 587. doi: 10.1038/s41557-019-0238-5
[101]	Liu, Y.-Z.; Ren, J.-X.; Wang, Y.-J.; Zhu, X.; Guan, X.-Y.; Wang, Z.-S.; Zhou, Y.-D.; Zhu, L.-K.; Qiu, S.-L.; Xiao, S.-X.; Fang, Q.-R. CCS Chem. 2022, 5, 2033. doi: 10.31635/ccschem.022.202202352
[102]	Valente, C.; Choi, E.; Belowich, M. E.; Doonan, C. J.; Li, Q.; Gasa, T. B.; Botros, Y. Y.; Yaghi, O. M.; Stoddart, J. F. Chem. Commun. 2010, 46, 4911. doi: 10.1039/c0cc00997k
[103]	Yan, Z.; Fang, L.; He, Z.; Xie, H.; Liu, B.; Guo, B.; Yao, Y. Small 2022, 18, 2200388. doi: 10.1002/smll.v18.21
[104]	Li, X.; Tang, H.; Gao, L.; Chen, Z.; Li, H.; Wang, Y.; Yang, K.; Lu, S.; Wang, K.; Zhou, Q.; Wang, Z. Polymer 2022, 241, 124474. doi: 10.1016/j.polymer.2021.124474
[105]	Becker, D.; Biswal, B. P.; Kaleńczuk, P.; Chandrasekhar, N.; Giebeler, L.; Addicoat, M.; Paasch, S.; Brunner, E.; Leo, K.; Dianat, A.; Cuniberti, G.; Berger, R.; Feng, X.-L. Chem. Eur. J. 2019, 25, 6562. doi: 10.1002/chem.v25.26
[106]	Cui, W.-R.; Zhang, C.-R.; Xu, R.-H.; Chen, X.-R.; Yan, R.-H.; Jiang, W.; Liang, R.-P.; Qiu, J.-D. ACS ES&T Water 2020, 1, 440.
[107]	Yang, L.; Yan, W.; Yang, N.; Wang, G.; Bi, Y.; Tian, C.; Liu, H.; Zhu, X. Small 2023, 2208118.
[108]	Zhang, F.; Dong, X.; Wang, Y.; Lang, X. Small 2023, 2302456.
[109]	Yang, Y.; Niu, H.; Xu, L.; Zhang, H.; Cai, Y. Appl. Catal., B 2020, 269, 118799. doi: 10.1016/j.apcatb.2020.118799
[110]	Zhai, L.; Yang, S.; Yang, X.; Ye, W.; Wang, J.; Chen, W.; Guo, Y.; Mi, L.; Wu, Z.; Soutis, C. Chem. Mater. 2020, 32, 9747. doi: 10.1021/acs.chemmater.0c03614
[111]	Xu, J.; Yang, C.; Bi, S.; Wang, W.; He, Y.; Wu, D.; Liang, Q.; Wang, X.; Zhang, F. Angew. Chem. Int. Ed. 2020, 59, 23845. doi: 10.1002/anie.v59.52
[112]	He, M.-H.; Ye, Z.-Q.; Lin, G.-Q.; Yin, S.; Huang, X.-Y.; Zhou, X.; Yin, Y.; Gui, B.; Wang, C. Acta Chim. Sinica 2023, 81, 784. (in Chinese) doi: 10.6023/A23040178
	(何明慧, 叶子秋, 林桂庆, 尹晟, 黄心翊, 周旭, 尹颖, 桂波, 汪成, 化学学报, 2023, 81, 784.) doi: 10.6023/A23040178
[113]	Chen, R.; Shi, J. L.; Ma, Y.; Lin, G.; Lang, X.; Wang, C. Angew. Chem. Int. Ed. 2019, 58, 6430. doi: 10.1002/anie.v58.19
[114]	Liu, X.; Qi, R.; Li, S.; Liu, W.; Yu, Y.; Wang, J.; Wu, S.; Ding, K.; Yu, Y. J. Am. Chem. Soc. 2022, 144, 23396. doi: 10.1021/jacs.2c09369
[115]	Huang, N.; Zhai, L.; Coupry, D. E.; Addicoat, M. A.; Okushita, K.; Nishimura, K.; Heine, T.; Jiang, D. Nat. Commun. 2016, 7, 12325. doi: 10.1038/ncomms12325 pmid: 27460607
[116]	Li, Z.; Deng, T.; Ma, S.; Zhang, Z.; Wu, G.; Wang, J.; Li, Q.; Xia, H.; Yang, S. W.; Liu, X. J. Am. Chem. Soc. 2023, 145, 8364.
[117]	Yu, X.-H.; Huang, W.; Li, Y.-G. Acta Chim. Sinica 2022, 80, 1494. (in Chinese) doi: 10.6023/A22070303
	(于潇涵, 黄伟, 李彦光, 化学学报, 2022, 80, 1494.) doi: 10.6023/A22070303
[118]	Yang, M.; Mo, C.; Fang, L.; Li, J.; Yuan, Z.; Chen, Z.; Jiang, Q.; Chen, X.; Yu, D. Adv. Funct. Mater. 2020, 30, 2000516. doi: 10.1002/adfm.v30.34
[119]	Yang, S.; Streater, D.; Fiankor, C.; Zhang, J.; Huang, J. J. Am. Chem. Soc. 2021, 143, 1061. doi: 10.1021/jacs.0c11719
[120]	Carrow, B. P.; Hartwig, J. F. J. Am. Chem. Soc. 2011, 133, 2116. doi: 10.1021/ja1108326 pmid: 21280669
[121]	Zhou, D.; Tan, X.; Wu, H.; Tian, L.; Li, M. Angew. Chem. Int. Ed. 2019, 58, 1376. doi: 10.1002/anie.v58.5
[122]	Zhang, Q.; Sun, Y.; Li, H.; Tang, K.; Zhong, Y.-W.; Wang, D.; Guo, Y.; Liu, Y. Research 2021, 2021, 9790705.

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

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

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

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

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

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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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

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.

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