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Chinese Journal of Organic Chemistry >

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

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

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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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

Cite this article

Xiao Tangxin , Zhou Ling , Wei Xiaoyan , Li Zhengyi , Sun Xiaoqiang . Supramolecular Copolymers Driven by Quadruple Hydrogen Bonding and Host-Guest Interactions[J]. Chinese Journal of Organic Chemistry, 2020 , 40(4) : 944 -949 . DOI: 10.6023/cjoc201911014

References

[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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