Recent Advances in Novel Macrocyclic Arenes

doi:10.6023/cjoc202005007

Abstract

Calixarenes, pillararenes and their analogues are composed of hydroxy-or alkoxy-substituted aromatic rings bridged by methylene or methenyl groups, which can be collectively called as macrocyclic arenes. Macrocyclic arenes have attracted much attention and increasing interests because of their unique structures, easily synthesis and derivatization, electron-rich cavities and wide applications in supramolecular chemistry, and they have also become one of the most significant and studied synthetic macrocyclic hosts during the last decades. Recently, with the rapid development of macrocycles and supramolecular chemistry, various types of novel macrocyclic arenes except the classic macrocyclic arenes such as calixarenes and pillararenes have been reported. The construction and functionalization of novel macrocyclic arenes have become the new focus and hot topic of macrocyclic and supramolecular chemistry. The recent advances in the synthesis and properties of novel macrocyclic arenes are summarized. It is expected that this review will be helpful to the research of macrocyclic arenes and promote the development of macrocyclic arene chemistry.

Key words: macrocyclic arene, synthesis, host-guest chemistry, self-assembly, supramolecular chemistry

Cite this article

Li Jing, Han Ying, Chen Chuanfeng. Recent Advances in Novel Macrocyclic Arenes[J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3714-3737.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Gutsche, C. D. Calixarenes Revisited, Royal Society of Chemistry, Cambridge, 1998.
[2] Sliwa, W.; Kozlowski, C. Calixarenes and Resorcinarenes:Synthesis, Properties and Applications, Wiley-VCH, Weinheim, Germany, 2009.
[3] Neri, P.; Sessler, J. L.; Wang, M.-X. Calixarenes and Beyond. Springer, Switzerland, 2016.
[4] Ogoshi, T.; Kanai, S.; Fujinami, S.; Yamagishi, T.-A.; Nakamoto, Y. J. Am. Chem. Soc. 2008, 130, 5022.
[5] Ogoshi, T. Pillararenes, The Royal Society of Chemistry, Croydon, UK, 2016.
[6] Chen, C.-F.; Han, Y. Acc. Chem. Res. 2018, 51, 2093.
[7] Schneebeli, S. T.; Cheng, C.; Hartlieb, K. J.; Strutt, N. L.; Sarjeant, A. A.; Stern, C. L.; Stoddart, J. F. Chem.-Eur. J. 2013, 19, 3860.
[8] Wang, J.-H.; Feng, H.-T.; Zheng, Y. S. Chem. Commun. 2014, 50, 11407.
[9] Han, B.; Zhu, L.; Wang, X.; Bai, M.; Jiang, J. Chem. Commun. 2018, 54, 837.
[10] Gao, B.; Tan, L.-L.; Song, N.; Li, K.; Yang, Y.-W. Chem. Commun. 2016, 52, 5804.
[11] Wu, J.-R.; Wang, C.-Y.; Tao, Y.-C.; Wang, Y.; Li, C.; Yang, Y.-W. Eur. J. Org. Chem. 2018, 1321.
[12] Dai, D.; Li, Z.; Yang, J.; Wang, C.; Wu, J.-R.; Wang, Y.; Zhang, D.; Yang, Y.-W. J. Am. Chem. Soc. 2019, 141, 4756.
[13] Boinski, T.; Cieszkowski, A.; Rosa, B.; Szumna, A. J. Org. Chem. 2015, 80, 3488.
[14] Hua, B.; Shao, L.; Zhou, J.; Yu, G. New J. Chem. 2016, 40, 4756.
[15] Zafrani, Y.; Cohen, Y. Org. Lett. 2017, 19, 3719.
[16] Wu, J.-R.; Mu, A. U.; Li, B.; Wang, C.-Y.; Fang, L.; Yang, Y.-W. Angew. Chem., Int. Ed. 2018, 57, 9853.
[17] Wang, X.; Wu, J.-R.; Liang, F.; Yang, Y.-W. Org. Lett. 2019, 21, 5215.
[18] Li, X.; Han, J.; Qin, J.; Sun, M.; Wu, J.; Lei, L.; Li, J.; Fang, L.; Yang, Y.-W. Chem. Commun. 2019, 55, 14099.
[19] Wu, J.-R.; Li, B.; Yang, Y.-W. Angew. Chem., Int. Ed. 2020, 59, 2251.
[20] Liu, Z.; Wu, J.; Wang, C.; Yang, J.; Wang, Y.; Yang, Y.-W. Chin. Chem. Lett. 2019, 30, 2299.
[21] Wu, J.-R.; Yang, Y.-W. J. Am. Chem. Soc. 2019, 141, 12280.
[22] Lei, S.-N.; Xiao, H.; Zeng, Y.; Tung, C.-H.; Wu, L.-Z.; Cong, H. Angew. Chem., Int. Ed. 2020, 59, 10059.
[23] Yang, W.; Samanta, K.; Wan, X.; Thikekar, T. U.; Chao, Y.; Li, S.; Du, K.; Xu, J.; Gao, Y.; Zuilhof, H.; Sue, A. C.-H. Angew. Chem., Int. Ed. 2020, 59, 3994.
[24] Chen, C.-F.; Ma, Y.-X. Iptycene Chemistry:From Synthesis to Applications, Springer-Verlag, Berlin Heidelberg, 2013.
[25] Han, Y.; Meng, Z.; Ma, Y.-X.; Chen, C.-F. Acc. Chem. Res. 2014, 47, 2026.
[26] Tian, X.-H.; Hao, X.; Liang, T.-L.; Chen, C.-F. Chem. Commun. 2009, 6771.
[27] Tian, X.-H.; Chen, C.-F. Chem.-Eur. J. 2010, 16, 8072.
[28] Xia, Y.-X.; Xie, T.; Han, Y.; Chen, C.-F. Org. Chem. Front. 2014, 1, 140.
[29] Li, P.-F.; Chen, C.-F. Chem. Commun. 2011, 47, 12170.
[30] Tian, X.-H.; Chen, C.-F. Org. Lett. 2010, 12, 524.
[31] Xia, Y.-X.; Han, Y.; Chen, C.-F. Eur. J. Org. Chem. 2014, 1976.
[32] Zhang, G.-W.; Li, P.-F.; Meng, Z.; Wang, H.-X.; Han, Y.; Chen, C.-F. Angew. Chem., Int. Ed. 2016, 55, 5304.
[33] Wang, J.-Q.; Li, J.; Zhang, G.-W.; Chen, C.-F. J. Org. Chem. 2018, 83, 11532.
[34] Zhang, G.-W.; Li, P.-F.; Wang, H.-X.; Han, Y.; Chen, C.-F. Chem.-Eur. J. 2017, 23, 3735.
[35] Zhang, G.-W.; Shi Q.; Chen, C.-F. Chem. Commun. 2017, 53, 2582.
[36] Shi, Q.; Han, Y.; Chen, C.-F. Chem.-Asian J. 2017, 12, 2576.
[37] Shi, Q.; Chen C.-F. Org. Lett. 2017, 19, 3175.
[38] Li, J.; Shi, Q.; Han, Y.; Chen, C.-F. Beilstein J. Org. Chem. 2019, 15, 1795.
[39] Zhang, G.-W.; Han, Y.-C.; Han, Y.; Wang, Y.-L.; Chen, C.-F. Chem. Commun. 2017, 53, 10433.
[40] Yang, X.; Mao, W.; Liu, Y.; Li, L.; Ma, D. Chin. J. Chem. 2019, 37, 575.
[41] Guo, Y.; Han, Y.; Chen, C.-F. Front. Chem. 2019, 7, 543.
[42] Shi, Q.; Meng, Z.; Xiang, J.-F.; Chen, C.-F. Chem. Commun. 2018, 54, 3536.
[43] Zhou, H.-Y.; Han, Y.; Shi, Q.; Chen, C.-F. Eur. J. Org. Chem. 2019, 3406.
[44] Zhou, H.-Y.; Han, Y.; Shi, Q.; Chen, C.-F. J. Org. Chem. 2019, 84, 5872.
[45] Shi, Q.; Chen, C.-F. Chem. Sci. 2019, 10, 2529.
[46] Chen, H.; Fan, J.; Hu, X.; Ma, J.; Wang, S.; Li, J.; Yu, Y.; Jia, X.; Li, C. Chem. Sci. 2015, 6, 197.
[47] Zhou, J.; Yu, G.; Shao, L.; Hua, B.; Huang, F. Chem. Commun. 2015, 51, 4188.
[48] Ma, J.; Deng, H.; Ma, S.; Li, J.; Jia, X.; Li, C. Chem. Commun. 2015, 51, 6621.
[49] Zhou, J.; Yang, J.; Zhang, Z.; Yu, G. RSC Adv. 2016, 6, 77179.
[50] Ma, S.; Chen, H.; Li, J.; Jia, X.; Li, C. Chem. Asian J. 2016, 11, 3449.
[51] Ma, J.; Meng, Q.; Hu, X.; Li, B.; Ma, S.; Hu, B.; Li, J.; Jia, X.; Li, C. Org. Lett. 2016, 18, 5740.
[52] Dai, L.; Ding, Z.-J.; Cui, L.; Li, J.; Jia, X.; Li, C. Chem. Commun. 2017, 53, 12096.
[53] Huang, X.; Zhang, X.; Qian, T.; Ma, J.; Cui, L.; Li, C. Beilstein J. Org. Chem. 2018, 14, 2236.
[54] Wang, Y.; Xu, K.; Li, B.; Cui, L.; Li, J.; Jia, X.; Zhao, H.; Fang, J.; Li, C. Angew. Chem., Int. Ed. 2019, 58, 10281.
[55] Li, B.; Wang, B.; Huang, X.; Dai, L.; Cui, L.; Li, J.; Jia, X.; Li, C. Angew. Chem., Int. Ed. 2019, 58, 3885.
[56] Xu, K.; Zhang, Z.-Y.; Yu, C.; Wang, B.; Dong, M.; Zeng, X.; Gou, R.; Cui, L.; Li, C. Angew. Chem., Int. Ed. 2020, 59, 7214.
[57] Zhou, J.; Yang, J.; Hua, B.; Shao, L.; Zhang, Z.; Yu, G. Chem. Commun. 2016, 52, 1622.
[58] Zhou, J.; Yu, G.; Li, Q.; Wang, M.; Huang, F. J. Am. Chem. Soc. 2020, 142, 2228.
[59] Yang, P.; Jian, Y.; Zhou, X.; Li, G.; Deng, T.; Shen, H.; Yang, Z.; Tian, Z. J. Org. Chem. 2016, 81, 2974.
[60] Li, G.; Zhao, L.; Yang, P.; Yang, Z.; Tian, Z.; Chen, Y.; Shen, H.; Hu, C. Anal. Chem. 2016, 88, 10751.
[61] Zhou, X.; Li, G.; Yang, P.; Zhao, L.; Deng, T.; Shen, H.; Yang, Z.; Tian, Z.; Chen, Y. Sens. Actuators B 2017, 242, 56.
[62] Li, G.; Song, X.; Yu, H.; Hu, C.; Liu, M.; Cai, J.; Zhao, L.; Chen, Y.; Yang, P. Sens. Actuators B 2018, 259, 177.
[63] Yang, Z.; Chen, Y.; Li, G.; Tian, Z.; Zhao, L.; Wu, X.; Ma, Q.; Liu, M.; Yang, P. Chem.-Eur. J. 2018, 24, 6087.
[64] Boinski, T.; Cieszkowski, A.; Rosa, B.; Lesniewska, B.; Szumna, A. New J. Chem. 2016, 40, 8892.
[65] Sala, P. D.; Regno, R. D.; Talotta, C.; Capobianco, A.; Hickey, N.; Geremia, S.; Rosa, M.D.; Spinella, A.; Soriente, A.; Neri, P.; Gaeta, C. J. Am. Chem. Soc. 2020, 142, 1752.
[66] Boinski, T.; Szumna, A. New J. Chem. 2017, 41, 3387.
[67] Han, X.-N.; Han, Y.; Chen, C.-F. J. Am. Chem. Soc. 2020, 142, 8262.

新型大环芳烃的研究进展