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2020 , Vol. 40 >Issue 4: 944 - 949

DOI: https://doi.org/10.6023/cjoc201911014

研究论文

利用四重氢键和主客体作用构筑超分子共聚物

  • 肖唐鑫 ,
  • 周玲 ,
  • 魏小艳 ,
  • 李正义 ,
  • 孙小强
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  • 常州大学石油化工学院 江苏常州 213164

收稿日期: 2019-11-07

  修回日期: 2019-11-30

  网络出版日期: 2019-12-19

基金资助

国家自然科学基金（Nos.21702020，21572026）资助项目.

收起

Supramolecular Copolymers Driven by Quadruple Hydrogen Bonding and Host-Guest Interactions

  • Xiao Tangxin ,
  • Zhou Ling ,
  • Wei Xiaoyan ,
  • Li Zhengyi ,
  • Sun Xiaoqiang
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  • School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164

Received date: 2019-11-07

  Revised date: 2019-11-30

  Online published: 2019-12-19

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21702020, 21572026).

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摘要

合成了一种同时含有脲基嘧啶酮基团（UPy）和苯并21冠7基团（B21C7）的单体H以及一种同时含有两个二烷基铵盐单元的单体G.分子H和G中的功能基团均由短间隔基相连.H可以通过四重氢键形成二聚体，进而和G发生主客体组装形成线性超分子共聚物.对该超分子共聚物进行了如下表征：随浓度变化1H NMR，粘度测试以及扫描电子显微镜（SEM）等.该结果将启发在更多领域中利用正交策略构筑各种超分子聚合物智能材料.

关键词： 超分子化学; 四重氢键; 自组装; 超分子聚合物; 冠醚; 大环; 主客体作用

本文引用格式

肖唐鑫 , 周玲 , 魏小艳 , 李正义 , 孙小强 . 利用四重氢键和主客体作用构筑超分子共聚物[J]. 有机化学, 2020 , 40(4) : 944 -949 . DOI: 10.6023/cjoc201911014

Abstract

A heteroditopic monomer (H) comprised of ureidopyrimidinone (UPy) group and benzo-21-crown-7 motif and a homoditopic monomer (G) containing two dialkylammonium salt units have been successfully prepared. The functional groups both in H and G are linked together by a short spacer. Through quadruple hydrogen bonds, H can self-assemble into dimers, which are capable of complexing with G via host-guest interaction to form linear supramolecular copolymers. The supramolecular copolymers were fully characterized by various techniques, such as concentration-dependent 1H NMR, viscosity measurements, and scanning electron microscope (SEM). The results will inspire the orthogonal construction of supramolecular polymers for smart materials in more fields.

Key words： supramolecular chemistry; quadruple hydrogen bonds; self-assembly; supramolecular polymer; crown ethers; macrocycles; host-guest interaction

参考文献

[1] Bandy, T. J.; Brewer, A.; Burns, J. R.; Marth, G.; Nguyen, T.; Stulz, E. Chem. Soc. Rev. 2011, 40, 138.
[2] McLaughlin, C. K.; Hamblin, G. D.; Sleiman, H. F. Chem. Soc. Rev. 2011, 40, 5647.
[3] Watson, J. D.; Crick, F. H. C. Nature 1953, 171, 737.
[4] Goor, O. J. G. M.; Hendrikse, S. I. S.; Dankers, P. Y. W.; Meijer, E. W. Chem. Soc. Rev. 2017, 46, 6621.
[5] Würthner, F.; Saha-Möller, C. R.; Fimmel, B.; Ogi, S.; Leowanawat, P.; Schmidt, D. Chem. Rev. 2016, 116, 962.
[6] Yang, L.; Tan, X.; Wang, Z.; Zhang, X. Chem. Rev. 2015, 115, 7196.
[7] Ma, X.; Tian, H. Acc. Chem. Res. 2014, 47, 1971.
[8] Yan, X.; Wang, F.; Zheng, B.; Huang, F. Chem. Soc. Rev. 2012, 41, 6042.
[9] Brunsveld, L.; Folmer, B. J.; Meijer, E. W.; Sijbesma, R. P. Chem. Rev. 2001, 101, 4071.
[10] Li, B.; Wang, B.; Huang, X.; Dai, L.; Cui, L.; Li, J.; Jia, X.; Li, C. Angew. Chem., Int. Ed. 2019, 58, 3885.
[11] Li, M, Han, K, Li, J, Jia X, Li C. Acta Polym. Sin. 2017, 129(in Chinese). (李明阳, 韩康, 李健, 贾学顺, 李春举, 高分子学报, 2017, 129.)
[12] Zheng, B.; Hou, Y.; Gao, L.; Zhang, M. Chin. J. Chem. 2019, 37, 843.
[13] Zhao, Y.-K.; Gao, Z.-Z.; Wang, H.; Zhang, D.-W.; Li, Z.-T. Chin. Chem. Lett. 2019, 30, 127.
[14] Chen, Y.; Sun, S.; Lu, D.; Shi, Y.; Yao, Y. Chin. Chem. Lett. 2019, 30, 37.
[15] Yin, G.; Chen, L.; Wang, C.; Yang, H. Chin. J. Chem. 2018, 36, 134.
[16] Xu, C.; Xu, L.; Ma, X. Chin. Chem. Lett. 2018, 29, 970.
[17] Wang, X.; Yang, Y.; Fan, L.; Yang, F.; Wu, D. Sci. China Chem. 2018, 61,311.
[18] Xiao, T.; Zhou, L.; Sun, X.-Q.; Huang, F.; Lin, C.; Wang, L. Chin. Chem. Lett. 2020, 31, 1.
[19] Wei, P.; Yan, X.; Huang, F. Chem. Soc. Rev. 2015, 44, 815.
[20] Elacqua, E.; Lye, D. S.; Weck, M. Acc. Chem. Res. 2014, 47, 2405.
[21] Li, S.-L.; Xiao, T.; Lin, C.; Wang, L. Chem. Soc. Rev. 2012, 41, 5950.
[22] Wang, Q.; Chen, Y.; Liu, Y. Polym. Chem. 2013, 4, 4192.
[23] Yan, X.; Xu, D.; Chi, X.; Chen, J.; Dong, S.; Ding, X.; Yu, Y.; Huang, F. Adv. Mater. 2012, 24, 362.
[24] Lu, C.; Zhang, M.; Tang, D.; Yan, X.; Zhang, Z.; Zhou, Z.; Song, B.; Wang, H.; Li, X.; Yin, S.; Sepehrpour, H.; Stang, P. J. J. Am. Chem. Soc. 2018, 140, 7674.
[25] Zhang, Z.; Liu, Y.; Zhao, J.; Yan, X. Polym. Chem. 2019, 11, 367.
[26] Wang, Q.; Cheng, M.; Tian, L.; Fan, Q.; Jiang, J. Polym. Chem. 2017, 8, 6058.
[27] Kim, D. S.; Chang, J.; Leem, S.; Park, J. S.; Thordarson, P.; Sessler, J. L. J. Am. Chem. Soc. 2015, 137, 16038.
[28] Hu, X.-Y.; Zhang, P.; Wu, X.; Xia, W.; Xiao, T.; Jiang, J.; Lin, C.; Wang, L. Polym. Chem. 2012, 3, 3060.
[29] Guan, Y.; Ni, M.; Hu, X.; Xiao, T.; Xiong, S.; Lin, C.; Wang, L. Chem. Comm. 2012, 48, 8529.
[30] Li, S.-L.; Xiao, T.; Wu, Y.; Jiang, J.; Wang, L. Chem. Commun. 2011, 47, 6903.
[31] Xu, L. N.; Chen, D.; Zhang, Q.; He, T.; Lu, C. J.; Shen, X.; Tang, D. T.; Qiu, H. Y.; Zhang, M. M.; Yin, S. C. Polym. Chem. 2018, 9, 399.
[32] Shangguan, L.; Xing, H.; Mondal, J. H.; Shi, B. Chem. Commun. 2017, 53, 889.
[33] Xiao, T.; Feng, X.; Wang, Q.; Lin, C.; Wang, L.; Pan, Y. Chem. Commun. 2013, 49, 8329.
[34] Beijer, F. H.; Sijbesma, R. P.; Kooijman, H.; Spek, A. L.; Meijer, E. W. J. Am. Chem. Soc. 1998, 120, 6761.
[35] Sijbesma, R. P.; Beijer, F. H.; Brunsveld, L.; Folmer, B. J. B.; Hirschberg, J. H. K. K.; Lange, R. F. M.; Lowe, J. K. L.; Meijer, E. W. Science 1997, 278, 1601.
[36] Xiao, T.; Zhong, W.; Qi, L.; Gu, J.; Feng, X.; Yin, Y.; Li, Z.-Y.; Sun, X.-Q.; Cheng, M.; Wang, L. Polym. Chem. 2019, 10, 3342.
[37] Xiao, T.; Xu, L.; Wang, J.; Li, Z.-Y.; Sun, X.-Q.; Wang, L. Org. Chem. Front. 2019, 6, 936.
[38] Yan, X.; Liu, Z.; Zhang, Q.; Lopez, J.; Wang, H.; Wu, H. C.; Niu, S.; Yan, H.; Wang, S.; Lei, T.; Li, J.; Qi, D.; Huang, P.; Huang, J.; Zhang, Y.; Wang, Y.; Li, G.; Tok, J. B.; Chen, X.; Bao, Z. J. Am. Chem. Soc. 2018, 140, 5280.
[39] Song, Y.; Liu, Y.; Qi, T.; Li, G. L. Angew. Chem., Int. Ed. 2018, 57, 13838.
[40] Liu, M.; Liu, P.; Lu, G.; Xu, Z.; Yao, X. Angew. Chem., Int. Ed. 2018, 57, 11242.
[41] Qin, B.; Zhang, S.; Song, Q.; Huang, Z.; Xu, J. F.; Zhang, X. Angew. Chem., Int. Ed. 2017, 56, 7639.
[42] Peng, H.-Q.; Zheng, X.; Han, T.; Kwok, R. T. K.; Lam, J. W. Y.; Huang, X.; Tang, B. Z. J. Am. Chem. Soc. 2017, 139, 10150.
[43] Lavrenova, A.; Balkenende, D. W. R.; Sagara, Y.; Schrettl, S.; Simon, Y. C.; Weder, C. J. Am. Chem. Soc. 2017, 139, 4302.
[44] Peng, H.-Q.; Sun, C.-L.; Niu, L.-Y.; Chen, Y.-Z.; Wu, L.-Z.; Tung, C.-H.; Yang, Q.-Z. Adv. Funct. Mater. 2016, 26, 5483.
[45] Fu, X.; Gu, R.-R.; Zhang, Q.; Rao, S.-J.; Zheng, X.-L.; Qu, D.-H.; Tian, H. Polym. Chem. 2016, 7, 2166.
[46] Xiao, T.; Xu, L.; Götz, J.; Cheng, M.; Wuerthner, F.; Gu, J.; Feng, X.; Li, Z.-Y.; Sun, X.; Wang, L. Mater. Chem. Front. 2019, 7, 1526-1540.
[47] Chen, J. Z.; Yan, X. Z.; Chi, X. D.; Wu, X. J.; Zhang, M. M.; Han, C. Y.; Hu, B. J.; Yu, Y. H.; Huang, F. H. Polym. Chem. 2012, 3, 3175.
[48] Yan, X.; Zhou, M.; Chen, J.; Chi, X.; Dong, S.; Zhang, M.; Ding, X.; Yu, Y.; Shao, S.; Huang, F. Chem. Commun. 2011, 47, 7086.
[49] Zhang, C.; Li, S.; Zhang, J.; Zhu, K.; Li, N.; Huang, F. Org. Lett. 2007, 9, 5553.
[50] Xu, L.; Shen, X.; Zhou, Z.; He, T.; Zhang, J.; Qiu, H.; Saha, M. L.; Yin, S.; Stang, P. J. J. Am. Chem. Soc. 2018, 140, 16920.
[51] Li, X.; Wang, L.; Deng, Y.; Luo, Z.; Zhang, Q.; Dong, S.; Han, C. Chem. Commun. 2018, 54, 12459.
[52] Zhang, M.; Yin, S.; Zhang, J.; Zhou, Z.; Saha, M. L.; Lu, C.; Stang, P. J. Proc. Natl. Acad. Sci. U. S. A. 2017, 114, 3044.
[53] Jiang, W.; Schäfer, A.; Mohr, P. C.; Schalley, C. A. J. Am. Chem. Soc. 2010, 132, 2309.
[54] Xiao, T. X.; Qi, L. J.; Zhong, W. W.; Lin, C.; Wang, R. B.; Wang, L. Y. Mater. Chem. Front. 2019, 3, 1973.
[55] Xiao, T.; Zhou, L.; Xu, L.; Zhong, W.; Zhao, W.; Sun, X.-Q.; Elmes, R. B. P. Chin. Chem. Lett. 2019, 30, 271.
[56] Xiao, T.; Zhong, W.; Zhou, L.; Xu, L.; Sun, X.-Q.; Elmes, R. B. P.; Hu, X.-Y.; Wang, L. Chin. Chem. Lett. 2019, 30, 31.
[57] Xiao, T.; Zhong, W.; Xu, L.; Sun, X.-Q.; Hu, X.-Y.; Wang, L. Org. Biomol. Chem. 2019, 17, 1336.
[58] Xiao, T.; Xu, L.; Zhou, L.; Sun, X.-Q.; Lin, C.; Wang, L. J. Mater. Chem. B 2019, 7, 1526.
[59] Xiao, T.; Wang, L. Tetrahedron Lett. 2018, 59, 1172.
[60] Yan, X.; Xu, D.; Chen, J.; Zhang, M.; Hu, B.; Yu, Y.; Huang, F. Polym. Chem. 2013, 4, 3312.
[61] Chen, Z.-Q.; Chen, T.; Liu, J.-X.; Zhang, G.-F.; Li, C.; Gong, W.-L.; Xiong, Z.-J.; Xie, N.-H.; Tang, B. Z.; Zhu, M.-Q. Macromolecules 2015, 48, 7823.
[62] Czech, A.; Czech, B. P.; Bartsch, R. A. J. Heterocycl. Chem. 1988, 25, 1841.
[63] Keizer, H. M.; Sijbesma, R. P.; Meijer, E. W. Eur. J. Org. Chem. 2004, 2553.
[64] Rao, M. L. N.; Dasgupta, P. Tetrahedron Lett. 2012, 53, 162.
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