有机多孔聚咔唑的制备及性能研究进展
收稿日期: 2015-02-11
网络出版日期: 2015-04-13
基金资助
项目受国家自然科学基金(Nos. 21274033, 21374024)和科技部国家重大科研项目(No. 2014CB932200)资助.
Recent Advance in Organic Porous Polycarbazoles: Preparation and Properties
Received date: 2015-02-11
Online published: 2015-04-13
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21274033 and 21374024) and the National Science and Technology Major Project of the Ministry of Science and Technology of China (No. 2014CB932200).
聚咔唑具有刚性主链和共轭富电子体系, 既有利于形成永久性多孔材料, 又可增强被吸附物与吸附剂之间的相互作用, 还具有特异的光电性能. 因此, 近年来有机多孔聚咔唑材料的研究成为有机多孔材料领域中的一个热点. 有机多孔聚咔唑一般具有较大的比表面积和稳定的孔结构, 其制备方法简单多样, 多孔性可调控, 而且可以保持良好的光学电学性质, 在气体存储与分离、有机蒸气吸附、催化、传感及有机电子学等方面具有潜在的应用价值. 就有机多孔聚咔唑材料的制备而言, 常用的制备方法是以氧化偶联反应和Friedel-Crafts反应为代表的合成方法, 还有一些如氰基三聚和碳–碳偶联反应等其他的合成方法. 本文主要介绍近几年有机多孔聚咔唑的制备方法和性能研究与应用方面的最新进展.
操强 , 陈琦 , 韩宝航 . 有机多孔聚咔唑的制备及性能研究进展[J]. 化学学报, 2015 , 73(6) : 541 -556 . DOI: 10.6023/A15020126
Polycarbazole has rigid backbone and conjugated electron rich system, which are beneficial to form permanent porous materials, enhance interactions between adsorbate and adsorbent, and exhibit intrinsic optical and electrical performance. As a novel kind of porous materials, organic porous polycarbazoles possess high specific surface area and permanent porosity, which have drawn great interests owing to the advantages in synthetic diversity, pore size controllability, optical and electrical properties. The preparation of organic porous polycarbazoles has recently been developed rapidly because of their great potential applications in gas storage, separation, vapor adsorption, catalysis, sensing and organic electronics. As for preparative methods of the organic porous polycarbazoles, carbazole-based oxidative coupling polymerization and Friedel-Crafts alkylation are the representative methods. Some other synthetic methods such as nitrile-based trimerization of aromatic nitriles and classic carbon-carbon coupling polymerization. Recently, a facile method for the preparation of hypercrosslinked organic porous polycarbazoles via FeCl3-promoted one-step oxidative coupling reaction and Friedel-Crafts alkylation in one pot has also been reported. According to the summarized results of porosity and adsorption performance, micro/mesoporous conjugated polycarbazole with high porosity can be obtained via molecular structure tuning. The Brunauer-Emmett-Teller specific surface area of porous polycarbazole is up to 2440 m2·g-1. The adsorption performance of some organic porous polycarbazoles not only can be comparable with that of the known porous organic polymers with ultrahigh specific surface area, such as PAF-1 and PNN-4, but also can be competitive with the best reported results for porous organic polymers, activated carbons, and metal-organic frameworks under the same conditions. Herein, recent advance such as synthetic methods, properties, and applications in organic porous polycarbazoles has been reviewed.
Key words： carbazole; porous organic polymer; preparation; property and application
[1] Schüth, F.; Sing, K. S. W.; Weitkamp, J. Handbook of Porous Solids, Wiley-VCH, Weinheim, 2002.
[2] Xiong, J.-F.; Xiao, P.; Wu, Q.; Wang, X.-Z.; Hu, Z. Acta Chim. Sinica 2014, 72, 433. (熊静芳, 肖佩, 吴强, 王喜章, 胡征, 化学学报, 2014, 72, 433.)
[3] Sui, D.; Huang, Y.; Huang, L.; Zhang, Y.; Chen, Y.-S. Acta Chim. Sinica 2014, 72, 382. (随东, 黄毅, 黄璐, 张昳, 陈永胜, 化学学报, 2014, 72, 382.)
[4] Xiang, Z.-H.; Cao, D.-P. J. Mater. Chem. A 2013, 1, 2691.
[5] Zhang, Y. G.; Riduan, S. N. Chem. Soc. Rev. 2012, 41, 2083.
[6] Ding, S.-Y.; Wang, W. Chem. Soc. Rev. 2013, 42, 548.
[7] Cooper, A. I. CrystEngComm 2013, 15, 1483.
[8] Feng, X.; Ding, X.-S.; Jiang, D.-L. Chem. Soc. Rev. 2012, 41, 6010.
[9] Cote, A. P.; Benin, A. I.; Ockwig, N. W.; Keeffe, O. M.; Matzger, A. J.; Yaghi, O. M. Science 2005, 310, 1166.
[10] Zhang, T.-T.; Wang, H.-T.; Ma, H.-P.; Sun, F.-X.; Cui, X.-Q.; Zhu, G.-S. Acta Chim. Sinica 2013, 71, 1598. (张婷婷, 王海涛, 马和平, 孙福兴, 崔小强, 朱广山, 化学学报, 2013, 71, 1598.)
[11] McKeown, N. B.; Budd, P. M. Macromolecules 2010, 43, 5163.
[12] McKeown, N. B.; Budd, P. M. Chem. Soc. Rev. 2006, 35, 675.
[13] Budd, P. M.; Ghanem, B. S.; Makhseed, S.; McKeown, N. B.; Msayib, K. J.; Tattershall, C. E. Chem. Commun. 2004, 230.
[14] Xu, Y.-H.; Jin, S.-B.; Xu, H.; Nagai, A.; Jiang, D.-L. Chem. Soc. Rev. 2013, 42 8012.
[15] Cooper, A. I. Adv. Mater. 2009, 21, 1291.
[16] Tsyurupa, M. P.; Davankov, V. A. React. Funct. Polym. 2006, 66, 768.
[17] Ben, T.; Qiu, S.-L. CrystEngComm 2013, 15, 17.
[18] Ben, T.; Ren, H.; Ma, S.-Q.; Cao, D.-P.; Lan, J.-H.; Jing, X.-F.; Wang, W.-C.; Xu, J.; Deng, F.; Simmons, J. M.; Qiu, S.-L.; Zhu, G.-S. Angew. Chem., Int. Ed. 2009, 48, 9457.
[19] Wang, W.; Yan, Z.-J.; Yuan, Y.; Sun, F.-X.; Zhao, M.; Ren, H.; Zhu, G.-S. Acta Chim. Sinica 2014, 72, 557. (王维, 闫卓君, 元野, 孙福兴, 赵明, 任浩, 朱广山, 化学学报, 2014, 72, 557.)
[20] Lu, W. G.; Yuan, D. Q.; Zhao, D.; Schilling, C. I.; Plietzsch, O.; Muller, T.; Bräse, S.; Guenther, J.; Blümel, J.; Krishna, R.; Li, Z.; Zhou, H. C. Chem. Mater. 2010, 22, 5964.
[21] Liu, D.-P.; Chen, Q.; Zhao, Y.-C.; Han, B.-H. Chin. Sci. Bull. 2013, 58, 2352. (刘德鹏, 陈琦, 赵彦超, 韩宝航, 科学通报, 2013, 58, 2352.)
[22] Zhao, Y.-C.; Chen, Q.; Han, B.-H. Sci. China Phys. Mech. Astron. 2011, 41, 1029. (赵彦超, 陈琦, 韩宝航, 中国科学: 物理学 力学 天文学, 2011, 41, 1029.)
[23] Haszeldine, R. S. Science 2009, 325, 1647.
[24] Dawson, R.; Laybourn, A.; Clowes, R.; Khimyak, Y. Z.; Adams, D. J.; Cooper, A. I. Macromolecules 2009, 42, 8809.
[25] Weber, J.; Thomas, A. J. Am. Chem. Soc. 2008, 130, 6334.
[26] Chen, Q.; Luo, M.; Hammershøj, P.; Zhou, D.; Han, Y.; Laursen, B. W.; Yan, C.-G.; Han, B.-H. J. Am. Chem. Soc. 2012, 134, 6084.
[27] Chen, Q.; Liu, D.-P.; Luo, M.; Feng, L.-J.; Zhao, Y.-C.; Han, B.-H. Small 2014, 10, 308.
[28] Chen, Q.; Liu, D.-P.; Zhu, J.-H.; Han, B.-H. Macromolecules 2014, 47, 5926.
[29] Feng, L.-J.; Chen, Q.; Zhu, J.-H.; Liu, D.-P.; Zhao, Y.-C.; Han, B.-H. Polym. Chem. 2014, 5, 3081.
[30] Qiao, S.-L.; Du, Z.-K.; Yang, R.-Q. J. Mater. Chem. A 2014, 2, 1877.
[31] Zhang, Y.-W.; Sigen, A.; Zou, Y.-C.; Luo, X.-L.; Li, Z.-P.; Xia, H.; Liu, X.-M.; Mu, Y. J. Mater. Chem. A 2014, 2, 13422.
[32] Zhang, X.; Lu, J.-Z.; Zhang, J. Chem. Mater. 2014, 26, 4023.
[33] Gu, C.; Chen, Y.-C.; Zhang, Z.-B.; Xue, S.-F.; Sun, S.-H.; Zhang, K.; Zhong, C.-M.; Zhang, H.-H.; Pan, Y.-Y.; Lv, Y.; Yang, Y.-Q.; Li, F.-H.; Zhang, S.-B.; Huang, F.; Ma, Y.-G. Adv. Mater. 2013, 25, 3443.
[34] Gu, C.; Huang, N.; Gao, J.; Xu, F.; Xu, Y.-H.; Jiang, D.-L. Angew. Chem., Int. Ed. 2014, 53, 4850.
[35] Katsoulidis, A. P.; Dyar, S. M.; Carmieli, R.; Malliakas, C. D.; Wasielewski, M. R.; Kanatzidis, M. G. J. Mater. Chem. A 2013, 1, 10465.
[36] Preis, E.; Widling, C.; Brunklaus, G.; Schmidt, J.; Thomas, A.; Scherf, U. ACS Macro. Lett. 2013, 2, 380.
[37] Zhu, J.-H.; Chen, Q.; Sui, Z.-Y.; Pan, L.; Yu, J.-G.; Han, B.-H. J. Mater. Chem. A 2014, 2, 16181.
[38] Pan, L.; Chen, Q.; Zhu, J.-H.; Yu, J.-G.; He, Y.-J.; Han, B.-H. Polym. Chem. 2015, 6, 2478.
[39] Zhu, X.; Mahurin, S. M.; An, S. H.; DoThanh, C.; Tian, C. C.; Li, T. K.; Gill, L. W.; Hagaman, E. W.; Bian, Z. J.; Zhou, J. H.; Hu, J.; Liu, H. L.; Dai, S. Chem. Commun. 2014, 50, 7933.
[40] Saleh, M.; Lee, H. M.; Kemp, K. C.; Kim, S. K. ACS Appl. Mater. Interfaces 2014, 6, 7325.
[41] Liu, Y.; Wu, S. F.; Wang, G.; Yu, G. P.; Guan, J. G.; Pan, C. Y.; Wang, Z. G. J. Mater. Chem. A 2014, 2, 7795.
[42] Wu, S. F.; Liu, Y.; Yu, G. P.; Guan, J. G.; Pan, C. Y.; Du, Y.; Xiong, X.; Wang, Z. G. Macromolecules 2014, 47, 2875.
[43] Liu, X. M.; Xu, Y. H.; Jiang, D. L. J. Am. Chem. Soc. 2012, 134, 8738.
[44] Schlapbach, L.; Zuttel, A. Nature 2001, 414, 353.
[45] Rabbani, M. G.; El-Kaderi, H. M. Chem. Mater. 2011, 23, 1650.
[46] Ghanem, B. S.; Hashem, M.; Harris, K. D. M.; Msayib, K. J.; Xu, M.; Budd, P. M.; Chaukura, N.; Book, D.; Tedds, S.; Walton, A.; McKeown, N. B. Macromolecules 2010, 43, 5287.
[47] Yuan, D. Q.; Lu, W. G.; Zhao, D.; Zhou, H. C. Adv. Mater. 2011, 23, 3723.
[48] Lu, W.; Yuan, D.; Sculley, J.; Zhao, D.; Krishna, R.; Zhou, H.-C. J. Am. Chem. Soc. 2011, 133, 18126.
[49] Ben, T.; Pei, C.; Zhang, D.; Xu, J.; Deng, F.; Jing, X.; Qiu, S. L. Energy Environ. Sci. 2011, 4, 3991.
[50] Dawson, R.; Stockel, E.; Holst, J. R.; Adams, D. J.; Cooper, A. I. Energy Environ. Sci. 2011, 4, 4239.
[51] Furukawa, H.; Yaghi, O. M. J. Am. Chem. Soc. 2009, 131, 8875.
[52] Texier-Mandoki, N.; Dentzer, J.; Piquero, T.; Saadallah, S.; David, P.; Vix-Guterl, C. Carbon 2004, 42, 2744.
[53] Yang, Z. X.; Xia, Y. D.; Mokaya, R. J. Am. Chem. Soc. 2007, 129, 1673.
[54] Latroche, M.; Surble, S.; Serre, C.; Mellot-Draznieks, C.; Llewellyn, P. L.; Lee, J. H.; Chang, J. S.; Jhung, S. H.; Ferey, G. Angew. Chem., Int. Ed. 2006, 45, 8227.
[55] Banerjee, R.; Phan, A.; Wang, B.; Knobler, C.; Furukawa, H.; O'Keeffe, M.; Yaghi, O. M. Science 2008, 319, 939.
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