Chinese Journal of Organic Chemistry >
Supramolecular Assemblies Based on Intramolecular Three-Center Hydrogen Bond and their Applications
Received date: 2020-05-20
Revised date: 2020-07-06
Online published: 2020-08-19
Supported by
the Doctoral Scientific Research Startup Foundation of Xinyang Normal University(18077); the Doctoral Scientific Research Startup Foundation of Xinyang Normal University(18072); the Key Scientific Research Project of Henan Provincial Higher Educational Institutions(19A150042)
The intramolecular three-center hydrogen bond is regarded as an efficient and reliable means to control molecular conformation, which can induce linear molecules to form specific conformations (folding, helix, expansion, zigzag, etc.). In this paper, the research progress on supramolecular assemblies based on different types of intramolecular three-center hydrogen bond is summarized in detail according to the kinds of hydrogen bonding atoms, such as O…H…O, S…H…X (X=N, O), N…H…X (X=N, O), F…H…X (X=F, O, N), and so on. More specifically, the synthesis of supramolecular assemblies is elaborated, including macrocyclic compounds, foldamers, porous helical compounds and molecular duplexes. Furthermore, their applications in promoting organic reactions, molecular recognition, transmembrane channels, molecular machines, soft materials are introduced. It is anticipated that this review can provide a useful reference for the synthesis and applications of the three-center hydrogel bond-based supramolecular assemblies.
Qiang Pei , Aixiang Ding , Jinjin Wu . Supramolecular Assemblies Based on Intramolecular Three-Center Hydrogen Bond and their Applications[J]. Chinese Journal of Organic Chemistry, 2021 , 41(1) : 105 -125 . DOI: 10.6023/cjoc202005053
| [1] | Pei Q. J. Xinyang Normal Univ. (Nat. Sci. Ed.), 2018, 31, 160. |
| [1] | ( 裴强, 信阳师范学院(自然科学版), 2018, 31, 160.). |
| [2] | Huang, G.B; Chen, Z.L.; Wei, X.S.; Chen, Y..; Li, X.Y.; Zhong, H.; Tan, M.X. Chin. J. Org. Chem. 2020, 40, 614. |
| [2] | ( 黄国保, 陈志林, 韦贤生, 陈钰, 李秀英, 仲辉, 谭明雄, 有机化学, 2020, 40, 614.). |
| [3] | Yang Y.; Dou D.D. Prog. Chem. 2014, 26, 706. |
| [3] | ( 杨勇, 窦丹丹, 化学进展, 2014, 26, 706.). |
| [4] | Pei Q.; Ding A.X. Prog. Chem. 2019, 31, 258. |
| [4] | ( 裴强, 丁爱祥, 化学进展, 2019, 31, 258.). |
| [5] | Jeffrey G.A.; Maluszynska H. Int. J. Biol. Macromol. 1982, 4, 173. |
| [6] | Taylor R.; Kennard O.; Versichel W. J. Am. Chem. Soc. 1984, 106, 244. |
| [7] | Albrecht G.; Corey R.B. J. Am. Chem. Soc. 1939, 61, 1087. |
| [8] | Jeffrey G.A.; Mitra J. J. Am. Chem. Soc. 1984, 106, 5546. |
| [9] | Zhang D.W.; Zhao X.; Hou J.L.; Li, Z, T. Chem. Rev. 2012, 112, 5271. |
| [10] | Zhang D.W.; Li Z.T. Chin. J. Org. Chem. 2012, 32, 2009. |
| [10] | ( 张丹维, 黎占亭, 有机化学, 2012, 32, 2009.). |
| [11] | Hu J.C.; Feng W.; Li X.H.; Yang L.Q.; Yuan L.H.; He L.; Gong B. Acta Phys.-Chim. Sin. 2010, 26, 1811. |
| [11] | ( 胡晋川, 冯文, 李向晖, 杨柳青, 袁立华, 何兰, 龚兵, 物理化学学报,2010, 26, 1811.). |
| [12] | Yang Y.A.; Feng W.; Yuan L.H. Chem. J. Chin. Univ. 2011, 32, 1950. |
| [12] | ( 杨永安, 冯文, 袁立华, 高学校化学学报, 2011, 32, 1950.). |
| [13] | Yamato K.; Kline M.; Gong B. Chem. Commun. 2012, 48, 12142. |
| [14] | Gong B.; Shao Z.F. Acc. Chem. Res. 2013, 46, 2856. |
| [15] | Si W.; Xin P.Y.; Li Z.T.; Hou J.L. Acc. Chem. Res. 2015, 48, 1612. |
| [16] | Li, Z T.Prog. Chem. 2011, 23, 1. |
| [17] | Zhang D.W.; Zhao X.; Li Z.T. Acc. Chem. Res. 2014, 47, 1961. |
| [18] | Liu C.Z.; Yan M.; Wang H.; Zhang D.W.; Li Z.T. ACS Omega 2018, 3, 5165. |
| [19] | Gong B. Acc. Chem. Res. 2012, 45, 2077. |
| [20] | Zhu J.; Parra R.D.; Zeng H.Q.; Skrzypczak-Jankun E.; Zeng X.C.; Gong B. J. Am. Chem. Soc. 2000, 122, 4219. |
| [21] | Parra R.D.; Zeng H.Q.; Zhu J.; Zheng C.; Zeng X.C.; Gong B. Chem.-Eur. J. 2001, 7, 4352. |
| [22] | Parra R.D.; Gong B.; Zeng X.C.J. Chem. Phys. 2001, 115, 6036. |
| [23] | Wang H.; Zhang Y.K.; Zou S.; Cao J.X.; Huang Q.F.; Wang Q.W.; Zhu J. Chin. J. Org. Chem. 2018, 38, 2060. |
| [23] | ( 王恒, 张宇坤, 邹胜, 曹金鑫, 黄晴菲, 王启卫, 朱槿, 有机化学, 2018, 38, 2060.). |
| [24] | Hu Z.Q.; Chen C.F. Chem. Commun. 2005, 41, 2445. |
| [25] | Li F.; Gan Q.; Xue L.; Wang Z.M.; Jiang H. Tetrahedron Lett. 2009, 50, 2367. |
| [26] | Li X.; Zhan C.L.; Wang Y.B.; Yao J.N. Chem. Commun. 2008, 44, 2444. |
| [27] | Zhu H.H.; He W.W.; Zhan C.L.; Li X.; Guan Z.S.; Guo F.Q.; Yao J.N. Tetrahedron 2011, 67, 8458. |
| [28] | Jiang H.; Léger J.M.; Guionneau P.; Huc I. Org. Lett. 2004, 6, 2985. |
| [29] | Berni E.; Dolain C.; Kauffmann B.; Léger J.M.; Zhan C.L.; Huc I. J. Org. Chem. 2008, 73, 2687. |
| [30] | Liu S.G.; Li Y.Z.; Zuo J.L.; You X.Z. Acta Crystallogr., Sect. E 2004, 60, o1527. |
| [31] | Tang H.Z.; Doerksen R.J.; Jones T.V.; Klein M.L.; Tew G.N. Chem. Biol. 2006, 13, 427. |
| [32] | Choi S.; Isaacs A.; Clements D.; Liu D.; Kim H.; Scott R.W.; Winkler J.D.; DeGrado W.F. Proc. Natl. Acad. Sci. U. S. A. 2009, 106, 6968. |
| [33] | Zhu Y.Y.; Wu J.; Li C.; Zhu J.; Hou J.L.; Li C.Z.; Jiang X.K.; Li Z.T. Cryst. Growth Des. 2007, 7, 1490. |
| [34] | Gan Q.; Bao C.Y.; Kauffmann B.; Grélard A.; Xiang J.F.; Liu S.H.; Huc I.; Jiang H. Angew. Chem. Int. Ed. 2008, 47, 1715. |
| [35] | Gan Q.; Li F.; Li G.P.; Kauffmann B.; Xiang J.F.; Huc I.; Jiang H. Chem. Commun. 2010, 46, 297. |
| [36] | Zhu J.; Wang X.Z.; Chen Y.Q.; Jiang X.K.; Chen X.Z.; Li Z.T. J. Org. Chem. 2004, 69, 6221. |
| [37] | Ferguson J.S.; Yamato K.; Liu R.; He L.; Zeng X.C.; Gong B. Angew. Chem. Int. Ed. 2009, 48, 3150. |
| [38] | Guo R.; Zhang L.; Wang H.; Zhang D.W.; Li Z.T. Polym. Chem. 2015, 6, 2382. |
| [39] | Hu Z.Q.; Chen C.F. Tetrahedron 2006, 62, 3446. |
| [40] | Lu Y.X.; Shi Z.M.; Li Z.T.; Guan Z.B. Chem. Commun. 2010, 46, 9019. |
| [41] | He L.; An Y.; Yuan L.H.; Yamato K.; Feng W.; Gerlitz O.; Zheng C.; Gong B. Chem. Commun. 2005, 41, 3788. |
| [42] | He L.; An Y.; Yuan L.H.; Feng W.; Li M.F.; Zhang D.C.; Yamato K.; Zheng C.; Zeng X.C.; Gong B. Proc. Natl. Acad. Sci. U. S. A. 2006, 103, 10850. |
| [43] | Du Z.Y.; Ren C.L.; Ye R.J.; Shen J.; Maurizot V.; Lu Y.J.; Wang J.; Zeng, H, Q. Chem. Commun. 2011, 47, 12488. |
| [44] | Bao C.Y.; Kauffmann B.; Gan Q.; Srinivas K.; Jiang H.; Huc I. Angew. Chem. Int. Ed. 2008, 47, 4153. |
| [45] | Shi Z.M.; Wu C.F.; Zhou T.Y.; Zhang D.W.; Zhao X.; Li Z.T. Chem. Commun. 2013, 49, 2673. |
| [46] | Shang J.; Gan Q.; Dawson S.J.; Rosu F.; Jiang H.; Ferrand Y.; Huc I. Org. Lett. 2014, 16, 4992. |
| [47] | Koppireddi S.; Liu C.Z.; Wang H.; Zhang D.W.; Li Z.T. CrystEngComm 2019, 21, 2626. |
| [48] | Gong B. Chem.-Eur. J. 2001, 7, 4336. |
| [49] | Zhang Y.F.; Yamato K.; Zhong K.; Zhu J.; Deng J.G.; Gong B. Org. Lett. 2008, 10, 4339. |
| [50] | Zhao Y.Y.; Connor A.L.; Sobiech T.A.; Gong B. Org. Lett. 2018, 20, 5486. |
| [51] | Hou J.L.; Shao X.B.; Chen G.J.; Zhou Y.X.; Jiang X.K.; Li Z.T. J. Am. Chem. Soc. 2004, 126, 12386. |
| [52] | Li C.; Wang G.T.; Yi H.P.; Jiang X.K.; Li Z.T.; Wang R.X. Org. Lett. 2007, 9, 1797. |
| [53] | Berl V.; Huc I.; Khoury R.G.; Krische M.J.; Lehn J.M. Nature 2000, 407, 720. |
| [54] | Shirude P.S.; Gillies E.R.; Ladame S.; Godde F.; Shin-ya K.; Huc I.; Balasubramanian S. J. Am. Chem. Soc. 2007, 129, 11890. |
| [55] | Zheng L.; Zhan Y.L.; Yu C.Y.; Huang F.; Wang Y.; Jiang H. Org. Lett. 2017, 19, 1482. |
| [56] | Zheng D.; Zheng L.; Yu C.Y.; Zhan Y.L.; Wang Y.; Jiang H. Org. Lett. 2019, 21, 2555. |
| [57] | Zheng D.; Yu C.Y.; Zheng L.; Zhan Y.L.; Jiang H. Chin. Chem. Lett. 2020, 31, 673. |
| [58] | Zhu Y.Y.; Yi H.P.; Li C.; Jiang X.K.; Li Z.T. Cryst. Growth Des. 2008, 8, 1294. |
| [59] | Zhu Y.Y.; Jiang L.; Li Z.T. CrystEngComm 2009, 11, 235. |
| [60] | Li C.; Ren S.F.; Hou J.L.; Yi H.P.; Zhu S.Z.; Jiang X.K.; Li Z.T. Angew. Chem. Int. Ed. 2005, 44, 5725. |
| [61] | Li C.; Zhu Y.Y.; Yi H.P.; Li C.Z.; Jiang X.K.; Li Z.T.; Yu Y.H. Chem.-Eur. J. 2007, 13, 9990. |
| [62] | Wang L.; Xiao Z.Y.; Hou J.L.; Wang G.T.; Jiang X.K.; Li Z.T. Tetrahedron 2009, 65, 10544. |
| [63] | You L.Y.; Chen S.G.; Zhao X.; Liu Y.; Lan W.X.; Zhang Y.; Lu H.J.; Cao C.Y.; Li Z.T. Angew. Chem., Int. Ed. 2012, 51, 1657. |
| [64] | Liu Y.H.; Zhang L.; Xu X.N.; Li Z.M.; Zhang D.W.; Zhao X.; Li Z.T. Org. Chem. Front. 2014, 1, 494. |
| [65] | Shang J.; Gallagher N.M.; Bie F.S.; Li Q.L.; Che Y.K.; Wang Y.; Jiang H. J. Org. Chem. 2014, 79, 5134. |
| [66] | Yuan L.H.; Feng W.; Yamato K.; Sanford A.R.; Xu D.G.; Guo H.; Gong B. J. Am. Chem. Soc. 2004, 126, 11120. |
| [67] | Yang Y.A.; Yuan L.H.; Hu J.C.; Zou S.L.; Feng W.; Gong B. Acta Phys.-Chim. Sin. 2010, 26, 1557. |
| [67] | ( 杨永安, 袁立华, 胡晋川, 邹树良, 冯文, 龚兵, 物理化学学报, 2010, 26, 1557.). |
| [68] | Yang Y.A.; Feng W.; Hu J.C.; Zou S.L.; Gao R.Z.; Yamato K.; Kline M.; Cai Z.H.; Gao Y.; Wang Y.B.; Li Y.B.; Yang Y.L.; Yuan L.H.; Zeng X.C.; Gong B. J. Am. Chem. Soc. 2011, 133, 18590. |
| [69] | Kline M.A.; Wei X.X.; Horner I.J.; Liu R.; Chen S.; Chen S.; Yung K.Y.; Yamato K.; Cai Z.H.; Bright F.V.; Zeng X.C.; Gong B. Chem. Sci. 2015, 6, 152. |
| [70] | Wu X.X.; Liu R.; Sathyamoorthy B.; Yamato K.; Liang G.X.; Shen L.; Ma S.F.; Sukumaran D.K.; Szyperski T.; Fang W.H.; He L.; Chen X.B.; Gong B. J. Am. Chem. Soc. 2015, 137, 5879. |
| [71] | Feng W.; Yamato K.; Yang L.Q.; Ferguson J.S.; Zhong L.J.; Zou S.L.; Yuan L.H.; Zeng X.C.; Gong B. J. Am. Chem. Soc. 2009, 131, 2629. |
| [72] | Wu X.X., Liang G.X., Ji G., Fun H.K., He L., Gong B. Chem. Commun. 2012, 48, 2228. |
| [73] | Qin B.; Chen X.Y.; Fang X.; Shu Y.Y.; Yip Y.K.; Yan Y.; Pan S.Y.; Ong W.Q.; Ren C.L.; Su H.B.; Zeng H.Q. Org. Lett. 2008, 10, 5127. |
| [74] | Qin B.; Sun C.; Liu Y.; Shen J.; Ye R.J.; Zhu J.; Duan X.F.; Zeng H.Q. Org. Lett. 2011, 13, 2270. |
| [75] | Xing L.; Ziener U.; Sutherland T.C.; Cuccia L.A. Chem. Commun. 2005, 41, 5751. |
| [76] | Zhu Y.Y.; Li C.; Li G.Y.; Jiang X.K.; Li Z.T. J. Org. Chem. 2008, 73, 1745. |
| [77] | Ernst J.T.; Becerril J.; Park H.S.; Yin H.; Hamilton A.D. Angew. Chem., Int. Ed. 2003, 42, 535. |
| [78] | Wu Z.Q.; Jiang X.K.; Zhu S.Z.; Li Z.T. Org. Lett. 2004, 6, 229. |
| [79] | Wu J.; Fang F.; Lu W.Y.; Hou J.L.; Li C.; Wu Z.Q.; Jiang X.K.; Li Z.T.; Yu Y.H. J. Org. Chem. 2007, 72, 2897. |
| [80] | Pei Q.; Tang Q.; Tan Z.L.; Lu Z.L.; He L.; Gong B. RSC Adv. 2017, 7, 22248. |
| [81] | Shi Y.D.; Tang Q.; Jiang Y.F.; Pei Q.; Tan H.W.; Lu Z.L.; Gong B. Chem. Commun. 2018, 54, 3719. |
| [82] | Li X.H.; Fang Y.Y.; Deng P.C.; Hu J.C.; Li T.; Feng W.; Yuan L.H. Org. Lett. 2011, 13, 4628. |
| [83] | Li X.H.; Jia Y.M.; Ren Y.; Wang Y.J.; Hu J.C.; Ma T.; Feng W.; Yuan L.H. Org. Biomol. Chem. 2013, 11, 6975. |
| [84] | Yang Y.; Yang Z.Y.; Yi Y.P.; Xiang J.F.; Chen C.F.; Wan L.J.; Shuai Z.G. J. Org. Chem. 2007, 72, 4936. |
| [85] | Lin J.B.; Xu X.N.; Jiang X.K.; Li Z.T. J. Org. Chem. 2008, 73, 9403. |
| [86] | Zhu Y.Y.; Wang G.T.; Li Z.T. Org. Biomol. Chem. 2009, 7, 3243. |
| [87] | Wang L.; Wang G.T.; Zhao X.; Jiang X.K.; Li Z.T. J. Org. Chem. 2011, 76, 3531. |
| [88] | Dolain C.; Zhan C.L.; Léger J.M.; Daniels L.; Huc I. J. Am. Chem. Soc. 2005, 127, 2400. |
| [89] | Yi H.P.; Wu J.; Ding K.L.; Jiang X.K.; Li Z.T. J. Org. Chem. 2007, 72, 870. |
| [90] | Zheng L.; Zheng D.; Wang Y.R.; Yu C.Y.; Zhang K.; Jiang H. Org. Biomol. Chem. 2019, 17, 9573. |
| [91] | Qin B.; Ren C.L.; Ye R.J.; Sun C.; Chiad K.; Chen X.Y.; Li Z.; Xue F.; Su H.B.; Chass G.A.; Zeng H.Q. J. Am. Chem. Soc. 2010, 132, 9564. |
| [92] | Hu J.C.; Chen L.; Ren Y.; Deng P.C.; Li X.W.; Wang Y.J.; Jia Y.M.; Luo J.; Yang X.S.; Feng W.; Yuan L.H. Org. Lett. 2013, 15, 4670. |
| [93] | Li Y.B.; Liu C.H.; Xie Y.Z.; Li X.; Fan X.L.; Yuan L.H.; Zeng Q.D. Chem. Commun. 2013, 49, 9021. |
| [94] | Hu J.C.; Chen L.; Shen J.; Luo J.; Deng P.C.; Ren Y.; Zeng H.Q.; Feng W.; Yuan L.H. Chem. Commun. 2014, 50, 8024. |
| [95] | Mao L.J.; Pan W.; Fu Y.H.; Chen L.X.; Xu M.; Ren Y.; Feng W.; Yuan L.H. Org. Lett. 2017, 19, 18. |
| [96] | Yi. Yi. H. P.; Shao, X. B.; Hou, J. L.; Li, C.; Jiang, X. K.; Li, Z. T.New J. Chem. 2005, 29, 1213. |
| [97] | Yi H.P.; Li C.; Hou J.L.; Jiang X.K.; Li Z.T. Tetrahedron 2005, 61, 7974. |
| [98] | Zheng L.; Zhan Y.L.; Ye L.; Zheng D.; Wang Y.; Zhang K.; Jiang H. Chem.-Eur. J. 2019, 25, 14162. |
| [99] | Helsel A.J.; Brown A.L.; Yamato K.; Feng W.; Yuan L.H.; Clements A.J.; Harding S.V.; Szabo G.; Shao Z.F.; Gong B. J. Am. Chem. Soc. 2008, 130, 15784. |
| [100] | Wei X.X.; Zhang G.Q.; Shen Y.; Zhong Y.L.; Liu R.; Yang N.; Al-mkhaizim F.Y.; Kline M.A.; He L.; Li M.F.; Lu Z.L.; Shao Z.F.; Gong B. J. Am. Chem. Soc. 2016, 138, 2749. |
| [101] | Xin P.Y.; Zhu P.P.; Su P.; Hou J.L.; Li Z.T. J. Am. Chem. Soc. 2014, 136, 13078. |
| [102] | Xin P.Y.; Zhang L.; Su P.; Hou J.L.; Li Z.T. Chem. Commun. 2015, 51, 4819. |
| [103] | Zhang K.D.; Zhao X.; Wang G.T.; Liu Y.; Zhang Y.; Lu H.J.; Jiang X.K.; Li Z.T. Angew. Chem., Int. Ed. 2011, 50, 9866. |
| [104] | Zhang K.D.; Zhao X.; Wang G.T.; Liu Y.; Zhang Y.; Lu H.J.; Jiang X.K.; Li Z.T. Tetrahedron 2012, 68, 4517. |
| [105] | Zhang K.D.; Zhou T.Y.; Zhao X.; Jiang X.K.; Li Z.T. Langmuir 2012, 28, 14839. |
| [106] | Gan Q.; Ferrand Y.; Bao C.Y.; Kauffmann B.; Grélard A.; Jiang H.; Huc I. Science 2011, 331, 1172. |
| [107] | Ferrand Y.; Gan Q.; Kauffmann B.; Jiang H.; Huc I. Angew. Chem., Int. Ed. 2011, 50, 7572. |
| [108] | Cai W.; Wang G.T.; Xu Y.X.; Jiang X.K.; Li Z.T. J. Am. Chem. Soc. 2008, 130, 6936. |
| [109] | Cai W.; Wang G.T.; Du P.; Wang R.X.; Jiang X.K.; Li Z.T. J. Am. Chem. Soc. 2008, 130, 13450. |
| [110] | You L.Y.; Wang G.T.; Jiang X.K.; Li Z.T. Tetrahedron, 2009, 65, 9494. |
| [111] | Wang G.T.; Zhao X.; Li Z.T. Tetrahedron 2011, 67, 48. |
| [112] | Ren C.L.; Xu S.Y.; Xu J.; Chen H.Y.; Zeng H.Q. Org. Lett. 2011, 13, 3840. |
| [113] | Zou S.L.; He L.T.; Zhang J.; He Y.Z.; Yuan L.H.; Wu L.X.; Luo J.; Wang Y.H.; Feng W. Org. Lett. 2012, 14, 3584. |
| [114] | Li X.W.; Li B.; Chen L.; Hu J.C.; Wen C.D.Y.; Zheng Q.D.; Wu L.X.; Zeng H.Q.; Gong B.; Yuan L.H. Angew. Chem., Int. Ed. 2015, 54, 11147. |
/
| 〈 |
|
〉 |
