本文介绍了杂杯芳烃和冠芳烃的研究起源,总结了杂杯芳烃和冠芳烃的设计与合成、构象和大环空腔结构特征,展示了杂杯芳烃和冠芳烃的分子识别和组装性质,概述了杂杯芳烃和冠芳烃在功能材料的制备中的应用,展望了大环超分子化学未来的发展方向。
Research history of heteracalixaromatics and coronarenes are introduced herein. The design and synthesis of heteracalixaromatics and coronarenes are summarized followed by the description of the macrocyclic conformation and cavity structures. Molecular recognition towards cations, anions and neutral guest species and property of molecular assembly of these macrocyclic hosts are presented. Applications of heteracalixaromatics and coronarenes in the fabrication of functional materials are also demonstrated briefly. The future perspectives of heteracalixaromatics and coronarenes in macrocyclic and supramolecular chemistry are discussed at last.
Contents
1 Introduction
2 Macrocyclic and supramolecular chemistry of heteracalixaromatics
2.1 Synthesis and functionalization of heteracalixaromatics and their structures
2.2 Molecular recognition and molecular assembly of heteracalixaromatics
2.3 Probing high valent organocopper chemistry using heteracalixaromatics as molecular tools
2.4 Miscellaneous applications of heteracalixaromatics
3 Macrocyclic and supramolecular chemistry of coronarenes
3.1 Synthesis and functionalization reactions of coronarenes
3.2 Structure of coronarenes
3.3 Property and application of coronarenes
4 Conclusion and outlook
[1] Wang M X. Chem. Commun., 2008, 39(21):4541.
[2] Wang M X. Acc. Chem. Res., 2012, 45:182.
[3] Wang D X, Wang M X. Azacalixaromatics in Calixarenes and Beyond, Eds. Neri P, Sessler J L, Wang M X. Springer, 2016,Chapter 14.
[4] Maes W, Dehaen W. Chem. Soc. Rev., 2008, 37:2393.
[5] Tsue H, Ishibashi K, Tamura R. Top. Heterocycl. Chem., 2008, 17:73.
[6] Katz J. Oxacalixarenes in Calixarenes and Beyond, Eds. Ner P, Sessler J L, Wang M X. Springer, 2016. Chapter 15.
[7] Gutsche C D, Calixarenes Revisited. Cambridge:The Royal Society of Chemistry, 1998.
[8] Wang M X, Zhang X H, Zheng Q Y. Angew. Chem. Int. Ed., 2004, 43:838.
[9] Wang M X, Yang H B. J. Am. Chem. Soc., 2004, 126:15412.
[10] Ren W S, Zhao L, Wang M X. J. Org. Chem., 2015, 80:9272.
[11] Wang Q Q, Luo N, Wang X D, Ao Y F, Chen Y F, Liu J M, Su C Y, Wang D X, Wang M X. J. Am. Chem. Soc., 2017, 139:635.
[12] Li J T, Wang L X, Wang D X, Zhao L, Wang M X. J. Org. Chem., 2014, 79:2178.
[13] (a) Mascal M, Armstrong A, Bartberger M D. J. Am. Chem. Soc., 2002, 124:6274.;
(b) Quinonero D, Garau C, Rotger C, Frontera A, Ballester P, Costa A, Deya P M. Angew. Chem. Int. Ed., 2002, 41:3389.;
(c) Alkorta I, Rozas I, Elguero J. J. Am. Chem. Soc., 2002, 124:8593.
[14] For reviews, see:(a) Wang D X, Wang M X. Chimia, 2011, 65:939.;
(b) Frontera A, Gamez P, Mascal M, Mooibroek T J, Reedijk J. Angew. Chem. Int. Ed., 2011, 50:9564.;
(c) Chifotides H T, Dunbar K R. Acc. Chem. Res.,2013, 46:894.;
(d) Ballester P. Acc. Chem. Res., 2013, 46:874.;
(e) Watt M M, Sollins M S, Johnson D W. Acc. Chem. Res., 2013, 46:955.;
(f) Jentzsch A V, Hennig A, Mareda J, Matile S. Acc. Chem. Res., 2013, 46:2791.;
(g) Giese M, Albrecht M, Rissanen K. Chem. Rev., 2015, 115:8867.
[15] (a) Berryman O B, Bryantsev V S, Stay D P, Johnson D W, Hay B P. J. Am. Chem. Soc., 2007, 129:48.;
(b) Hay B P, Bryantsev V S. Chem. Commun., 2008, 39(21):2417.;
(c) Berryman O B, Johnson D W. Chem. Commun., 2009, 40(22):3143.
[16] Wang D X, Zheng Q Y, Wang Q Q, Wang M X. Angew. Chem. Int. Ed., 2008, 47:7485.
[17] Wang D X, Wang Q Q, Han Y, Wang Y, Huang Z T, Wang M X. Chem. Eur. J., 2010, 16:13053.
[18] Wang D X, Wang M X. J. Am. Chem. Soc., 2013, 135:892.
[19] (a) Gong H Y, Wang D X, Zheng Q Y, Wang M X. Tetrahedron, 2009, 65:87.;
(b) Fang Y X, Ao Y F, Wang D X, Zhao L, Wang M X. Tetrahedron, 2015, 71:2105.
[20] Gong H Y, Zheng Q Y, Zhang X H, Wang D X, Wang M X. Org. Lett., 2006, 8:4895.
[21] Fa S X, Chen X F, Yang S, Wang D X, Zhao L, Chen E Q, Wang M X. Chem. Commun., 2015, 51:5112.
[22] (a) Wu J C, Zhao L, Wang D X, Wang M X. Inorg. Chem., 2012, 51:3860.;
(b) Wu J C, Zhao L, Wang D X, Wang M X. Chinese J. Chem. 2013, 31:589.
[23] Gao C Y, Zhao L, Wang M X. J. Am. Chem. Soc., 2011, 133:8448.
[24] Gao C Y, Zhao L, Wang M X. J. Am. Chem. Soc., 2012, 134:824.
[25] (a) Fa S X, Wang L X, Wang D X, Zhao L, Wang M X. J. Org. Chem., 2014, 79:3559.;
(b) Wang L X, Zhao L, Wang D X, Wang M X. Chem. Commun., 2011, 47:9690.
[26] For recent review articles and research examples, see:(a) Allen S E, Walvood R R, Padilla-Salinas R, Kozlowski M C. Chem. Rev., 2013, 113:6234.;
(b) McCann S D, Stahl S S. Acc. Chem. Res.. 2015, 48:1756.;
(c) Li J D, Chen G S, Tan Z. Adv. Synth. Catal., 2016, 358:1174.;
(d) Zhang W, Wang F, McCann S D, Wang D H, Chen P H, Stahl S S, Liu G S. Science, 2016, 353:1014.;
(e) Chen X, Hao X S, Goodhue C E, Yu J Q. J. Am. Chem. Soc., 2006, 128:6790.;
(f) Wendlandt A E, Suess A M, Stahl S S. Angew. Chem. Int. Ed., 2011, 5:11062.;
(g) Phipps R J, Grimster N P, Gaunt M J. J. Am. Chem. Soc., 2008, 130:8172.;
(h) Chen B, Hou X L, Li Y X, Wu Y D. J. Am. Chem. Soc., 2011, 133:7668.;
(i) King A E, Huffman L M, Casitas A, Costas M, Ribas X, Stahl S S. J. Am. Chem. Soc., 2010, 132:12068.
[27] Yao B, Wang D X, Huang Z T, Wang M X. Chem. Commun., 2009, 110(20):2899.
[28] Zhang H,Yao B, Zhao L, Wang D X,Xu B Q, Wang M X. J. Am. Chem. Soc., 2014, 136:6326.
[29] (a) Yao B, Wang Z L, Zhang H, Wang D X, Zhao L, Wang M X. J. Org. Chem., 2012, 77:3336.;
(b) Long C, Zhang L, You J S, Wang M X. Organometallics, 2014, 33:1061.
[30] Wang Z L, Zhao L, Wang M X. Org. Lett., 2001, 13:6560.
[31] Liu Y, Zhang Q, Guo Q H, Wang M X. J. Org. Chem., 2016, 81:10404.
[32] Wang F, Zhao L, You J S, Wang M X. Org. Chem. Front., 2016, 3:880.
[33] Wang Z L, Zhao L, Wang M X. Chem. Commun., 2012, 48:9418.
[34] Wang Z L, Zhao L, Wang M X. Org. Lett., 2012,14:1472.
[35] Zhang H, Zhao L, Wang D X, Wang M X. Org. Lett., 2013, 15:3836.
[36] Zhang Q, Wang M X. Org. Chem. Front., 2017, 4:283.
[37] Yao B, Liu Y, Zhao L, Wang D X, Wang M X. J. Org. Chem., 2014, 79:11139.
[38] Liu Y, Long C, Zhao L, Wang M X. Org. Lett., 2016, 18:5078.
[39] (a) Tsue H, Ishibashi K, Tokita S, Takahashi H, Matsui K, Tamura R. Chem. Eur. J., 2008, 14:6125.;
(b) Tsue H, Matsui K, Ishibashi K, Takahashi H, Tokita S, Ono K, Tamura R. J. Org. Chem., 2008, 73:7748.;
(c) Tsue H, Ono K, Tokita S, Ishibashi K, Matsui K, Takahashi H, Miyata K, Takahashi D, Tamura R. Org. Lett., 2011, 13:490.;
(d) Tsue H, Takahash H, Ishibashi K, Inoue R, Shimizu S, Takahashi D, Tamura R. CrystEngComm, 2012, 14:1021.
[40] (a) Zhao W J, Wang W J, Chang H, Cui S W, Hu K, He L J, Lu K, Liu J X, Wu Y J, Qian J, Zhang S S. J. Chromatogr. A, 2012, 1251:74.;
(b) Zhang W F, Zhang Y H, Jiang Q, Zhao W J, Yu A J, Chang H, Lu X M, Xie F W, Ye B X, Zhang S S. Anal. Chem., 2016, 88:10523.
[41] (a) Uchida N, Kuwabara J, Taketosh A, Kanbara T. J. Org. Chem.,2012, 77:10631.;
(b) Uchida N, Taketoshi A, Kuwabara J, Yamamoto T, Inoue Y, Watanabe Y, Kanbara T. Org. Lett., 2010, 12:5242.
[42] He Q, Ao Y F, Huang Z T, Wang D X. Angew. Chem. Int. Ed., 2015, 54:11785.
[43] (a) Ma M L, Li X Y, Wen K. J. Am. Chem. Soc., 2009, 131:8338.;
(b) Li X Y, Liu L Q, Ma M L, Zhao X L, Wen K. Dalton Trans., 2010, 39:8646.
[44] (a) Wang H X, Meng Z, Xiang J F, Xia Y X, Sun Y, Hu S Z, Chen H, Yao J, Chen C F. Chem. Sci., 2016, 7:469.;
(b) Liu H, Hu W J, Liu Y A, Li J S, Jiang B, Wen K. J. Org. Chem., 2016, 81:6457.
[45] Guo Q H, Fu Z D, Zhao L, Wang M X. Angew. Chem. Int. Ed., 2014, 53:13548.
[46] Lu Y, Fu Z D, Guo G H, Wang M X. Org. Lett., 2017, 19:1590.
[47] Guo Q H, Zhao L, Wang M X. Chem. Eur. J., 2016, 22:6947.
[48] Fu Z D, Guo Q H, Zhang L, Wang D X, Wang M X. Org. Lett., 2016, 18:2668.
[49] Wu Z C, Guo G H, Wang M X. Angew. Chem. Int. Ed., 2017, 56:7151.
[50] Franke J, Vögtle F. Tetrahedron Lett., 1984, 25:3445.
[51] Takeuchi D, Asano I, Osakada K. J. Org. Chem., 2006, 71:8614.
[52] Kaplan K L, Reents W D. Tetrahedron Lett., 1982, 23:373.
[53] Sergeev V A, Nedel'kin V I, Astankov A V, Nikiforov A V, Alov E M, Moskvichev Y A. Bull. Acad. Sci. USSR, 1990, 39:763.
[54] Tsuchida E, Miyatake K, Yamamoto K, Hay A S. Macromolecules, 1998, 31:6469.
[55] (a) Baxter I, Ben-Haida A, Colquhoun H M, Hodge P, Kohnke F H, Williams D J. Chem. Eur. J., 2000, 6:4285.;
(b) Ben-Haida A, Colquhoun H M, Hodge P, Raftery J, White A J P, Williams D J. Org. Biomol. Chem., 2009, 7:5229.
[56] Ren W S, Zhao L, Wang M X. Org. Lett., 2016, 18:3126.
[57] Ren W S, Wang M X. Supramol. Chem., 2018, 30(7):583.
[58] Guo Q H, Zhao L, Wang M X. Angew. Chem. Int. Ed., 2015, 54:8386.
[59] Zhao M Y, Wang D X, Wang M X. J. Org. Chem., 2018, 83:1502.
[60] Zhao M Y, Guo Q H, Wang M X. Org. Chem. Front., 2018, 5:760.