含CH基的阴离子受体

伍宏伟; 陈亚运; 饶才辉; 刘传祥*

doi:10.7536/PC160532

化学进展 ›› 2016, Vol. 28 ›› Issue (10) :1501-1514 DOI: 10.7536/PC160532

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含CH基的阴离子受体

伍宏伟, 陈亚运, 饶才辉, 刘传祥*

作者信息 +

Anion Receptors Based on CH Donor Group

Wu Hongwei, Chen Yayun, Rao Caihui, Liu Chuanxiang*

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文章历史 +

摘要

阴离子在生命、临床及环境科学中有着重要作用，设计用于识别阴离子的人工合成受体是超分子化学的一个研究热点。识别阴离子的方法主要有氢键作用、质子转移机制、路易斯酸碱作用、以及基于不可逆的特定化学反应等。相对于传统的含NH或OH识别位点的阴离子受体，近年来含CH基阴离子受体的研究取得了长足的进展。本文详细评述了含烷基CH，苯基CH，三唑CH，咪唑鎓CH，三唑鎓CH以及CHCN基阴离子受体的设计、结构及其阴离子识别作用的研究进展。

Abstract

The design and synthesis of artificial receptors for sensing and recognition of anions have received considerable attention in supramolecular chemistry because of the essential roles that anions play in a wide variety of biological, clinical and environmental sciences. The usual design strategies for anion sensing are through hydrogen-bonding interaction, intermolecular proton-transfer reaction, the Lewis acid/base interactions or an irreversible specific chemical reaction. Compared to the conventional anion receptors containing the NH or OH binding sites, recently, the anion receptors based on CH group have attracted much attention. Therefore, this review summarizes the main design principles and sensing abilities of the anion receptors based on receptors which having alkyl CH groups, phenyl CH groups, triazole-based CH groups, imidazolium-based CH groups, triazolium-based CH groups, CHCN group.

Contents
1 Introduction
2 Alkyl-based CH groups
3 Phenyl-based CH groups
4 Triazole-based CH groups
5 Imidazolium-based CH groups
6 Triazolium-based CH groups
7 CHCN-based CH groups
8 Conclusion

Graphical abstract

关键词

阴离子受体 / CH基 / 氢键 / 阴离子

Key words

anion receptors / CH group / hydrogen bonds / anions

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伍宏伟, 陈亚运, 饶才辉, 刘传祥*. 含CH基的阴离子受体[J]. 化学进展, 2016, 28(10): 1501-1514 DOI:10.7536/PC160532

Wu Hongwei, Chen Yayun, Rao Caihui, Liu Chuanxiang*. Anion Receptors Based on CH Donor Group[J]. Progress in Chemistry, 2016, 28(10): 1501-1514 DOI:10.7536/PC160532

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参考文献

原文顺序 | 出版日期 | 本文引用

[1] Bianchi E, Bowman-James K, García-España E. Superamolecular Chemistry of Anions, New York:Wiley-VCH, 1997.
[2] 刘育(Liu Y),尤成才(You C C),张衡益(Zhang H Y).超分子化学——合成受体的分子识别与组装(Supramolecular Chemistry, Molecular Recognition and Assembly of Synthetic Receptors).天津:南开大学出版社(Tianjin:Nankai University Press), 2003.
[3] Xie Y, Morimoto T, Furuta H. Angew. Chem. Int. Ed.,2006, 45:6907.
[4] Amendola V, Fabbrizzi L, Mosca L. Chem. Soc. Rev., 2010, 39:3889.
[5] Li A, Wang J, Wang F, Jiang Y. Chem. Soc. Rev., 2010, 39:3729.
[6] Wang Q, Xie Y, Ding Y, Li X, Zhu W. Chem. Commun., 2010, 46:3669.
[7] Cai J, Sessler J L. Chem. Soc. Rev., 2014, 43:305.
[8] 吴芳英(Wu F Y), 温珍昌(Wen Z Z), 江云宝(Jiang Y B). 化学进展(Progress in Chemistry), 2004, 16(5):776.
[9] 林奇(Lin Q), 魏太保(Wei T B), 姚虹(Yao H), 张有明(Zhang Y M). 化学进展(Progress in Chemistry), 2009, 21(6):1207.
[10] Cai J, Sessler J L. Chem. Soc. Rev., 2014, 43:6198.
[11] Farnham W B, Roe D C, Dixon D A, Calabrese J C, Harlow R L. J. Am. Chem. Soc., 1990, 112:7707.
[12] Zhu S S, Staats H, Brandhorst K, Grunenberg J, Gruppi F, Dalcanale E, Lützen A, Rissanen K, Schalley C A. Angew.Chem. Int. Ed., 2008, 47:788.
[13] Bedford R B, Betham M, Butts C P, Coles S J, Hursthouse M B, Scully P N, Tucker J H R, Wilkie J, Willener Y. Chem. Commun., 2008, 2429.
[14] Pandian T S, Cho S J, Kang J. J. Org. Chem., 2013, 78:12121.
[15] García H M, Morales D, Pérez J, Puerto M, Río I. Chem. Eur. J., 2014, 20:5821.
[16] Sabater P, Zapata F, Caballero A, Fernándze I, Arellano C R, Molina P. J. Org. Chem., 2016, 81:3790.
[17] Hay B P,Gutowski M, Dixon D A, Garza J, Vargas R, Moyer B A. J. Am. Chem. Soc., 2004, 126:7925.
[18] Vargas R, Garza J, Dixon D A, Hay B P. J. Am. Chem. Soc., 2000, 122:4750.
[19] Graul S T, Squires R R. J. Am. Chem. Soc., 1990, 112:2517.
[20] Davico G E, Bierbaum V M, DePuy C H, Ellison G B, Squires R R. J. Am. Chem. Soc., 1995, 117:2590.
[21] Berryman O B, Sather A C, Hay B P, Meisner J S, Johnson D W. J. Am. Chem. Soc., 2008, 130:10895.
[22] Amendola V, Bergamaschi G, Boiocchi M, Fabbrizzi L, Milani M. Chem. Eur. J., 2010, 16:4368.
[23] Tresca B W, Zakharov L N, Carroll C N, Johnson D W, Haley M M. Chem. Commun., 2013, 49:7240.
[24] Lee S, Chen C H, Flood A H. Nat. Chem., 2013, 5:704.
[25] Tresca B W, Hansen R J, Chau C V, Hay B P, Zakharov L N, Haley M M, Johnson D W. J. Am. Chem. Soc., 2015, 137:14959.
[26] Xu L, Li Y, Li Y. Asian J. Org. Chem., 2014, 3:582.
[27] Li Y, Flood A H. Angew. Chem. Int. Ed., 2008, 47:2649.
[28] Li Y, Pink M, Karty JA, Flood A H. J. Am. Chem. Soc., 2008, 130:17293.
[29] Lee S, Hua Y, Park H, Flood A H. Org. Lett., 2010, 12:2100.
[30] McDonald K P, Ramabhadran R O, Lee S, Raghavachari K, Flood A H. Org. Lett., 2011, 13:6260.
[31] Ramabhadran R O, Liu Y, Hua Y, Ciardi M, Flood A H, Raghavachari K. J. Am. Chem. Soc., 2014, 136:5078.
[32] Meudtner R M, Hecht S. Angew. Chem. Int. Ed., 2008, 47:4926.
[33] Fisher M G, Gale P A, Hiscock J R, Hursthouse M B, Light M E, Schmidtchen F P, Tong C C. Chem. Commun., 2009, 3017.
[34] Sessler J L, Cai J, Gong H Y, Yang X, Arambula J F, Hay B P. J. Am. Chem. Soc., 2010, 132:14058.
[35] Cao Q Y, Pradhan T, Kim S, Kim J S. Org. Lett., 2011, 13:4386.
[36] Xu L, Li Y, Yu Y, Liu T, Cheng S, Liu H, Li Y. Org. Biomol. Chem., 2012, 10:4375.
[37] Li Y J, Xu L, Yang W L, Liu H B, Lai S W, Che C M, Li Y L. Chem. Eur. J., 2012, 18:4782.
[38] Cao L, Jiang R, Zhu Y, Wang X, Li Y, Li Y. Eur. J. Org. Chem., 2014, 2687.
[39] Kwon J Y, Singh N J, Kim H N, Kim S K, Kim S K, Yoon J Y. Am. Chem. Soc., 2004, 126:8892.
[40] Chellappan K, Singh N J, Hwang I C, Lee J W, Kim K S. Angew. Chem. Int. Ed., 2005, 44:2899.
[41] Zhou H, Zhao Y, Gao G, Li S, Lan J, You J. J. Am. Chem. Soc., 2013, 135:14908.
[42] Zhuo J B, Lin C X, Wan Q, Xie L L, Yuan Y F. J. Organomet. Chem., 2015, 791:289.
[43] Pandian T S, Kang J. Tetra. Let., 2015, 56:4191.
[44] Kumar A, Pandey P S. Org. Lett., 2008, 10:165.
[45] Schulze B, Friebe C, Hager M D, Günther W, Köhn U, Jahn B O, Görls H, Schubert S. Org. Lett., 2010, 12:2710.
[46] Cai J, Hay B P, Young N J, Yang X, Sessler J L. Chem. Sci., 2013, 4:1560.
[47] Zaapata F, Gonzale L, Caballero A, Alkorta I, Elguero J, Molina P. Chem. Eur. J., 2015, 21:9797.
[48] González L, Zapata F, Caballero A, Molina P, Arellano C R, Alkorta I, Elguero J. Chem. Eur. J., 2016, 22:7533.
[49] Chen J, Liu C, Zhang J, Ding W, Zhou M, Wu F. Chem. Commun., 2013, 49:10814.
[50] Li B, Zhang C, Liu C, Chen J, Wang X, Liu Z, Yi F. RSC Adv., 2014, 4:46016.
[51] Zhou M, Chen J, Liu C, Fu H, Zheng N, Zhang C, Chen Y, Cheng J.Chem. Commun., 2014, 50:14748.
[52] Zhang C, Liu C, Li B, Chen J, Zhang H, Hu Z, Yi F. New J. Chem., 2015, 51:8173.
[53] Liu C, Wang X, Wu H, Chen Y. Dyes and Pigments, 2016, 133:255.