Linear and Cross-Linked Supramolecular Polymers Based on a Dibenzo-24-crown-8 Bridged Pillar[5]arene Dimer

doi:10.6023/cjoc201811003

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (7): 1990-1995.DOI: 10.6023/cjoc201811003 Previous Articles Next Articles

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基于二苯并24-冠-8桥联双柱[5]芳烃的线性和网状超分子聚合物

霍博超, 李斌, 苏杭, 曾宪强, 徐凯迪, 崔雷

上海大学化学系上海 200444

收稿日期:2018-11-01 修回日期:2019-01-22 发布日期:2019-03-29
通讯作者: 崔雷 E-mail:cuilei@shu.edu.cn
基金资助:
国家自然科学基金（Nos.21772118，21472122）资助项目.

Linear and Cross-Linked Supramolecular Polymers Based on a Dibenzo-24-crown-8 Bridged Pillar[5]arene Dimer

Huo Bochao, Li Bin, Su Hang, Zeng Xianqiang, Xu Kaidi, Cui Lei

Department of Chemistry, Shanghai University, Shanghai 200444

Received:2018-11-01 Revised:2019-01-22 Published:2019-03-29
Contact: 10.6023/cjoc201811003 E-mail:cuilei@shu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21772118, 21472122).

1. Linear and Cross-Linked Supramolecular Polymers Based on a Dibenzo-24-crown-8 Bridged Pillar[5]arene Dimer.PDF(2750KB)

Abstract

One hybrid host molecule of dibenzo-24-crown-8 bridged pillar[5]arene dimer (1) was designed and synthesized. The combination of host 1 and ditopic guest 2 containing two 5-(1H-1,2,3-triazol-1-yl)pentanenitrile (TAPN) binding sites could afford linear AA/BB-type supramolecular polymers based on TAPN•pillar[5]arene recognition motif. Further introduction of ditopic guest 3 containing two secondary ammonium parts yields cross-linked supramolecular polymers through the host-guest inclusion between dibenzo-24-crown-8 and secondary ammonium salt. The supramolecular polymers were characterized by various techniques such as ¹H NMR, viscosity, DOSY and SEM, indicating that the formation of these supramolecular polymer was concentration-dependent. The critical polymerization concentration (CPC) of the formation of linear supramolecular polymers in chloroform/acetone (V:V=4:1) solutions is 28 mmol/L. This work provides a new strategy for the fabrication of novel supramolecular aggregates based on orthogonal host-guest interactions of hybrid macrocycles.

Key words: supramolecular polymer, crown ether, pillararene, hybrid host

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Huo Bochao, Li Bin, Su Hang, Zeng Xianqiang, Xu Kaidi, Cui Lei. Linear and Cross-Linked Supramolecular Polymers Based on a Dibenzo-24-crown-8 Bridged Pillar[5]arene Dimer[J]. Chin. J. Org. Chem., 2019, 39(7): 1990-1995.

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[1] Fouquey, C.; Lehn, J. M.; Levelut, A. M. Adv. Mater. 1990, 2, 254.
[2] Wijnands, S. P. W.; Engelen, W.; Lafleur, R. P. M.; Meijer, E. W.; Merkx, M. Nat. Commun. 2018, 9, 65.
[3] Zhou, Z.; Yan, X.; Cook, T. R.; Saha, M. L.; Stang, P. J. J. Am. Chem. Soc. 2016, 13, 806.
[4] Hu, X.; Zhang, P.; Wu, X.; Xia, W.; Xiao, T.; Jiang, J.; Lin, C.; Wang, L. Polym. Chem. 2012, 3, 3060.
[5] Xu, J.; Zhang, X. Acta Polym. Sin. 2017, 1, 37(in Chinese). (徐江飞, 张希, 高分子学报, 2017, 1, 37.)
[6] Huang, W.; Zhan, T.; Lin, F.; Zhao X. Prog. Chem. 2016, 28, 165(in Chinese). (黄文忠, 占田广, 林沨, 赵新, 化学进展, 2016, 28, 165.)
[7] Yang, L.; Tan, X.; Wang, Z.; Zhang, X. Chem. Rev. 2015, 115, 7196.
[8] Pedersen, C. J. J. Am. Chem. Soc. 1967, 89, 2495.
[9] Yan, X.; Xu, D.; Chen, J.; Zhang, M.; Hu, B.; Yu, Y.; Huang, F. Polym. Chem. 2013, 4, 3312.
[10] Cheng, S.-C.; Chen, K.-J.; Suzaki, Y.; Tsuchido, Y.; Kuo, T.-S.; Osakada, K.; Horie, M. J. Am. Chem. Soc. 2017, 140, 90.
[11] Chen, K.-J.; Tsai, Y.-C.; Suzaki, Y.; Osakada, K.; Miura, A.; Horie, M. Nat. Commun. 2016, 7, 13321.
[12] Miyauchi, M.; Harada, A. J. Am. Chem. Soc. 2004, 126, 11418.
[13] Liu, Y.; Song, S.-H.; Chen, Y.; Zhao, Y.-L.; Yang, Y.-W. Chem. Commun. 2005, 13, 1702.
[14] Zhang, Q.; Qu, D.-H.; Ma, X.; Tian, H. Chem. Commun. 2013, 49, 9800.
[15] Zhang, Q.; Qu, D.-H.; Wu, J.; Ma, X.; Wang, Q.; Tian, H. Langmuir 2013, 29, 5345.
[16] Guo, Q.-H.; Fu, Z.-D.; Zhao, L.; Wang, M.-X. Angew. Chem., Int. Ed. 2014, 53, 13548.
[17] Qian, H.; Guo, D.-S.; Liu, Y. Asian J. Org. Chem. 2012, 1, 155.
[18] Yao, X.; Ma, X.; Tian, H. J. Mater. Chem. C 2014, 2, 5155.
[19] Guo, D.; Zhang, T.; Wang, Y.; Liu, Y. Chem. Commun. 2013, 49, 6779.
[20] Villari, V.; Gattuso, G.; Notti, A.; Pappalardo, A.; Micali, N. J. Phys. Chem. B 2012, 116, 5537.
[21] Liu, Y.; Liu, K.; Wang, Z.; Zhang, X. Chem. Eur. J. 2011, 17, 9930.
[22] Harada, A.; Takashima, Y.; Yamaguchi, H. Chem. Soc. Rev. 2009, 38, 875.
[23] Ogoshi, T.; Kayama, H.; Yamafuji, D.; Aoki, T.; Yamagishi, T. A. Chem. Sci. 2012, 3, 3221.
[24] Li, C.; Han, K.; Li, J.; Zhang, Y.; Chen, W.; Yu, Y.; Jia, X. Chem. Eur. J. 2013, 19, 11892.
[25] Nan, S.; Takahiro, K.; Tada-Aki, Y.; Yang, Y.-W.; Tomoki, O. Chem 2018, 4, 2029.
[26] Yan, X.; Wang, F.; Zheng, B.; Huang, F. Chem. Soc. Rev. 2012, 41, 6042.
[27] Wei, P.; Yan, X.; Huang, F. Chem. Soc. Rev. 2012, 44, 815.
[28] Lou, X.-Y.; Yang, Y.-W. Adv. Opt. Mater. 2018, 6, 1800668.
[29] Wu, X.; Duan, Q.; Ni, M.; Hu, X.; Wang, L. Chin. J. Org. Chem. 2014, 34, 437(in Chinese). (吴旋, 段群鹏, 倪梦飞, 胡晓玉, 王乐勇, 有机化学, 2014, 34, 437.)
[30] 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.)
[31] Liu, Y.; Yang, Y.-W.; Li, L.; Chen, Y. Org. Biomol. Chem. 2004, 2, 1542.
[32] Li, S.-L.; Xiao, T.; Hu, B.; Zhang, Y.; Zhao, F.; Ji, Y.; Yu, Y.; Lin, C.; Wang, L. Chem. Commun. 2011, 47, 10755.
[33] Wang, K.; Guo, D.; Zhao, H.; Liu, Y. Chem. Eur. J. 2014, 20, 4023.
[34] Guo, D.-S.; Chen, K.; Zhang, H.-Q.; Liu, Y. Chem. Asian J. 2009, 4, 436.
[35] Zhao, H.; Guo, D.; Wang, L.; Qian, H.; Liu, Y. Chem. Commun. 2012, 48, 11319.
[36] Li, H.; Wang, J.; Ni, Y.; Zhou, Y.; Yan, D. Acta Chim. Sinica 2016, 74, 415(in Chinese). (李惠梅, 王洁, 倪云洲, 周永丰, 颜德岳, 化学学报, 2016, 74, 415.)
[37] Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T. A.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022.
[38] Ogoshi, T.; Takashima, S.; Yamagishi, T. J. Am. Chem. Soc. 2015, 137, 10962.
[39] Li, C. Chem. Commun. 2014, 50, 12420.
[40] Kakuta, T.; Yamagishi, T.; Ogoshi, T. Acc. Chem. Res. 2018, 51, 1656.
[41] Mirzaei, S.; Wang, D.; Lindeman, S. V.; Sem, C. M.; Rathore, R. Org. Lett. 2018, 20, 6583.
[42] Trinh, T. M.; Nierengarten, I.; Holler, M. Chem. Eur. J. 2015, 21, 8019.
[43] Hu, W.-B.; Yang, H.-M.; Hu, W.-J.; Ma, M.-L.; Zhao, X.-L.; Mi, X.-Q.; Liu, Y.; Li, J.-S.; Jiang, B.; Wen, K. Chem. Commun. 2014, 50, 10460.
[44] Li, C.; Zhao, L.; Li, J; Ding, X.; Chen, S.; Zhang, Q.; Yu, Y.; Jia, X. Chem. Commun. 2010, 46, 9016.
[45] Li, Z.-Y.; Zhang, Y.; Zhang, C.-W.; Chen, L.-J.; Wang, C.; Tan, H.; Yu, Y.; Li, X.; Yang, H.-B. J. Am. Chem. Soc. 2014, 136, 8577.
[46] Li, C.; Xu, Q.; Li, J.; Yao, F.; Jia, X. Org. Biomol. Chem. 2010, 8, 1568.
[47] Sun, Y.; Guo, F.; Zuo, T.; Hua, J.; Diao, G. Nat. Commun. 2016, 7, 12042.
[48] Wang, Y.; Ping, G.; Li, C. Chem. Commun. 2016, 52, 9858.
[49] Wheate, N. J.; Dickson, K. A.; Kim, R. R.; Nematollahi, A.; Macquart, R. B.; Kayser, V.; Yu, G. C.; Bret Church, W.; Marsh, D. J. J. Pharm. Sci. 2016, 105, 3615.
[50] Li, B.; Meng, Z.; Li, Q.; Huang, X.; Kang, Z.; Dong, H.; Chen, J.; Sun, J.; Dong, Y.; Li, J.; Jia, X.; Sessler, J. L.; Meng, Q.; Li, C. Chem. Sci. 2017, 8, 4458.
[51] Huerta, E.; Metselaar, G. A.; Fragoso, A.; Santos, E.; Bo, C.; De, M. J. Angew. Chem., Int. Ed. 2007, 46, 202.
[52] Zhang, Z.; Luo, Y.; Chen, J.; Dong, S.; Yu, Y.; Ma, Z.; Huang, F. Angew. Chem., Int. Ed. 2011, 50, 1397.
[53] Wang, C.; Lv, M.-Z.; Song, N.; Liu, Z.-J.; Wang, C.; Yang, Y.-W. Macromolecules 2017, 50, 5759.
[54] Song, N.; Chen, D.; Xia, M.-C.; Qiu, X.-L.; Ma, K.; Xu, B.; Tian, W.; Yang, Y.-W. Chem. Commun. 2015, 51, 5526.
[55] Wang, K.; Wang, C.-Y.; Wang, Y.; Li, H.; Bao, C.-Y.; Liu, J.; Zhang, S. X.-A.; Yang, Y.-W. Chem. Commun. 2013, 49, 10528.
[56] Shao, L.; Sun, J.; Hua, B.; Huang, F. Chem. Commun. 2018, 54, 4866.
[57] Khairou, K.; Hassan, R. Eur. Polym. J. 2000, 36, 2021.
[58] Song, N.; Chen, D.-X.; Qiu, Y.-C.; Yang, X.-Y.; Xu, B.; Tian, W.; Yang, Y.-W. Chem. Commun. 2014, 50, 8231.
[59] Li, C.; Chen, S.; Li, J.; Han, K.; Xu, M.; Hu, B.; Yu, Y.; Jia, X. Chem. Commun. 2011, 47, 11294.
[60] Han, K.; Zhang, Y.; Li, J.; Yu, Y.; Jia, X.; Li, C. Eur. J. Org. Chem. 2013, 11, 2057.
[61] Li, C.; Han, K.; Li, J.; Zhang, H.; Ma, J.; Shu, X.; Chen, Z.; Weng, L.; Jia, X. Org. Lett. 2012, 14, 42.
[62] Shu, X.; Chen, W.; Hou, D.; Meng, Q.; Zheng, R.; Li, C. Chem. Commun. 2014, 50, 4820.
[63] Wang, X.; Han, K.; Li, J.; Jia, X.; Li, C. Polym. Chem. 2013, 4, 3998.
[64] Söntjens, S. H. M.; Sijbesma, R. P.; van Genderen, M. H. P.; Meijer, E. W. Macromolecules 2001, 34, 3815.
[65] Xu, H.; Rudkevich, D. M. Chem. Eur. J. 2010, 10, 5432.

基于二苯并24-冠-8桥联双柱[5]芳烃的线性和网状超分子聚合物

Linear and Cross-Linked Supramolecular Polymers Based on a Dibenzo-24-crown-8 Bridged Pillar[5]arene Dimer

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