基于芳香分子-糖类手性超分子组装体及功能

王克让

doi:10.7536/PC150312

化学进展 ›› 2015, Vol. 27 ›› Issue (6) :775-784 DOI: 10.7536/PC150312

综述与评论

扫码查看或转发全文

基于芳香分子-糖类手性超分子组装体及功能

^1,2

作者信息 +

Chiral Supramolecular Assemblies Based on Aromatic Molecules-Carbohydrate Conjugates and Their Applications

Wang Kerang*^1,2

Author information +

文章历史 +

摘要

手性超分子组装体广泛存在于自然界中,因其在材料、化学和生物学等领域广阔的应用前景,引起了科学家们极大的兴趣。其中以糖类分子作为手性源,经分子自组装构筑手性超分子组装体的研究已成为超分子化学领域的研究热点之一。本文综述了基于糖类修饰的苝酰亚胺分子、偶氮苯分子、联苯类分子和卟啉类分子等芳香分子化合物经自组装构筑的手性超分子组装体,介绍了其在有机溶剂和水的混合溶剂、水中的凝胶性质,超分子手性特征和功能,糖分子类型与超分子组装体手性间的关系等,并对基于糖类的手性超分子组装体的前景进行了展望。

Abstract

In nature, helical self-assembly by non-covalent interactions is a widely observed feature. Inspired by the unique features of fascinating chiral superstructures, chemists have paid more attention to design numerous helical supramolecular assemblies. In them, carbohydrates as a natural source of chirality have been widely investigated in the construction of chiral supramolecular assembly, which possessed potential application in materials, chemistry and biology. This review aims to overview of the chiral supramolecular assembly based on aromatic molecules-carbohydrate conjugates, including perylene bisimides, azobenzene, poly(p-phenylene), porphyrins, and so on. Their gel properties, supramolecular chirality and functionalization in the mixtures of organic solution and water, or in water, and the relationship between their supramolecular chirality and the type of the carbohydrates are described. Furthermore, the potential application and future development of the chiral supramolecular assembly based on carbohydrates are discussed.

Contents
1 Introduction
2 Chiral supramolecular assembly based on perylene bisimides-carbohydrate conjugates
2.1 Solvent controlled supramolecular assembly
2.2 Substituent controlled supramolecular assembly in the bay position
2.3 Temperature controlled supramolecular assembly
2.4 Water soluble supramolecular assembly
3 Chiral supramolecular assembly based on azobenzene-carbohydrate conjugates
4 Chiral supramolecular assembly based on poly(p-phenylene)-carbohydrate conjugates
5 Chiral supramolecular assembly based on porphyrin-carbohydrate conjugates
6 Chiral supramolecular assembly based on other aromatic molecules-carbohydrate conjugates
7 Conclusion

Graphical abstract

关键词

手性 / 超分子组装体 / 糖类 / 自组装 / 苝酰亚胺

Key words

chirality / supramolecular assembly / carbohydrate / self-assembly / perylene bisimide

引用本文

引用格式 ▾

王克让. 基于芳香分子-糖类手性超分子组装体及功能[J]. 化学进展, 2015, 27(6): 775-784 DOI:10.7536/PC150312

Wang Kerang. Chiral Supramolecular Assemblies Based on Aromatic Molecules-Carbohydrate Conjugates and Their Applications[J]. Progress in Chemistry, 2015, 27(6): 775-784 DOI:10.7536/PC150312

登录浏览全文

4963

注册一个新账户忘记密码

参考文献

原文顺序 | 出版日期 | 本文引用

[1] Mackenzie K R. Chem. Rev., 2006, 106: 1931.
[2] Hannah K, Armitage B A. Acc. Chem. Res., 2004, 37: 845.
[3] Wang Y, Xu J, Wang Y W, Chen H Y. Chem. Soc. Rev., 2013, 42: 2930.
[4] Lim Y B, Moon K S, Lee M. Chem. Soc. Rev., 2009, 38: 925.
[5] 袁菁 (Yuan J), 张莉 (Zhang L), 黄昕 (Huang X), 姜思光(Jiang S G), 刘鸣华 (Liu M H). 化学进展 (Progress in Chemistry), 2005, 17: 780.
[6] 靳清贤 (Jin Q X), 李晶 (Li J), 李孝刚 (Li X G), 张莉(Zhang L), 方少明 (Fang S M), 刘鸣华 (Liu M H). 化学进展 (Progress in Chemistry), 2014, 26: 919.
[7] Kim H J, Kim T, Lee M. Acc. Chem. Res., 2011, 44: 72.
[8] Palmer L C, Stupp S I. Acc. Chem. Res., 2008, 41: 1674.
[9] Ryu J H, Hong D J, Lee M. Chem. Commun., 2008, 9: 1043.
[10] Kim Y, Li W, Shin S, Lee M. Acc. Chem. Res., 2013, 46: 2888.
[11] Dube D H, Bertozzi C R. Nat. Rev. Drug Discov., 2005, 4: 477.
[12] Ohtsubo K, Marth J D. Cell, 2006, 126: 855.
[13] Kim B S, Hong D J, Bae J, Lee M. J. Am. Chem. Soc., 2005, 127: 16333.
[14] Kim B S, Yang W Y, Ryu J H, Yoo Y S, Lee M. Chem. Commun., 2005, 15: 2035.
[15] Lee D W, Kim T, Park II S, Huang Z, Lee M. J. Am. Chem. Soc., 2012, 134: 14722.
[16] Ryu J H, Lee E, Lim Y B, Lee M. J. Am. Chem. Soc., 2007, 129: 4808.
[17] Kim T, Lee H, Kim Y, Nam J M, Lee M. Chem. Commun., 2013, 49: 3949.
[18] Lim Y B, Lee M. Org. Biomol. Chem., 2007, 5: 401.
[19] John G, Masuda M, Okada Y, Shimizu T. Adv. Mater., 2001, 13: 715.
[20] Jung J H, John G, Yoshida K, Shimizu T. J. Am. Chem. Soc., 2002, 124: 10674.
[21] Jung J H, Do Y, Lee Y A, Shimizu T. Chem. Eur. J., 2005, 11: 5538.
[22] Jung J H, John G, Masuda M, Yoshida K, Shinkai S, Shimizu T. Langmuir, 2001, 17: 7229.
[23] John G, Jung J H, Minamikawa H, Yoshida K, Shimizu T. Chem. Eur. J., 2002, 8: 5494.
[24] Vemula P K, Aslam U, Mallia V A, John G. Chem. Mater., 2007, 19: 138.
[25] Vemula P K, John G. Acc. Chem. Res., 2008, 41: 769.
[26] Shimizu T, Masuda M, Minamikawa H. Chem. Rev., 2005, 105: 1401.
[27] Würthner F. Chem. Commun., 2004, 14: 1564.
[28] Schenning A P H J, Herrikhuyzen J V, Jonkheijm P, Chen Z J, Würthner F, Meijer E W. J. Am. Chem. Soc., 2002, 124: 10252.
[29] Krieg E, Rybtchinski B. Chem. Eur. J., 2011, 17: 9016.
[30] Ho R M, Li M C, Lin S C, Wang H F, Lee Y D, Hasegawa H, Thomas E. J. Am. Chem. Soc., 2012, 134: 10974.
[31] Kumar M, George S J. Chem. Sci., 2014, 5: 3025.
[32] Seki T, Asano A, Seki S, Kikkawa Y, Murayama H, Karatsu T, Kitamura A, Yagai S. Chem. Eur. J., 2011, 17: 3598.
[33] Stepaneko V, Li X Q, Gershberg J, Würthner F. Chem. Eur. J., 2013, 19: 4176.
[34] Dehm V, Chen Z J, Baumeister U, Prins P, Siebbeles L D A, Würthner F. Org. Lett., 2007, 9: 1085.
[35] Ke D M, Tang A L, Zhan C L, Yao J N. Chem. Commun., 2013, 49: 4914.
[36] Kumar J, Nakashima T, Tsumatori H, Mori M, Naito M, Kawai T. Chem. Eur. J., 2013, 19: 14090.
[37] Kumar J, Nakashima T, Kawai T. Langmuir, 2014, 30: 6030.
[38] Huang Y W, Hu J C, Kuang W F, Wei Z X, Faul C F J. Chem. Commun., 2011, 47: 5554.
[39] Huang Y W, Wang J C, Wei Z X. Chem. Commun., 2014, 50: 8343.
[40] Hu J C, Kuang W F, Deng K, Zou W J, Huang Y W, Wei Z X, Faul C F J. Adv. Funct. Mater., 2012, 22: 4149.
[41] Guo Q, Wang J C, Zhu L Y, Wei Z X. Chin. J. Chem., 2015, 33: 95.
[42] Huang Y W, Wang J C, Zhai H Y, Zhu L Y, Wei Z X. Soft Mater., 2014, 10: 7920.
[43] Sun K, Xiao C Y, Liu C M, Fu W X, Wang Z H, Li Z B. Langmuir, 2014, 30: 11040.
[44] Wang K R, An H W, Wu L, Zhang J C, Li X L. Chem. Commun., 2012, 48: 5644.
[45] Wang K R, An H W, Wang Y Q, Zhang J C, Li X L. Org. Biomol. Chem., 2013, 11: 1007.
[46] Wang K R, An H W, Rong R X, Cao Z R, Li X L. Biosens. Bioelectron., 2014, 58: 27.
[47] Wang K R, Han D, Cao G J, Li X L. Chem. Asian J., 2015, 10: 1204.
[48] Samanta A, Stuart M C A, Ravoo B J. J. Am. Chem. Soc., 2012, 134: 19909.
[49] Srinivas O, Mitra N, Surolia A, Jayaraman N. J. Am. Chem. Soc., 2002, 124: 2124.
[50] Weber T, Chandrasekaran V, Stamer I, Thygesen M B, Terfort A, Lindhorst T K. Angew. Chem. Int. Ed., 2014, 53: 14583.
[51] Kobayashi H, Friggri A, Koumoto K, Amaike M, Shinkai S, Reinhoudt D N. Org. Lett., 2002, 4: 1423.
[52] Kobayashi H, Koumoto K, Jung J H, Shinkai S. J. Chem. Soc. Perkin Trans. 2, 2002, 1930.
[53] Ogawa Y, Yoshiyama C, Kitaoka T. Langmuir, 2012, 28: 4404.
[54] Clemente M J, Tejedor R M, Romero P, Fitremann J, Oriol L. RSC Adv., 2012, 2: 11419.
[55] Rajaganesh R, Gopal A, Das T M, Ajayaghosh A. Org. Lett., 2012, 14: 748.
[56] Cui J, Liu A, Guan Y, Zheng J, Shen Z, Wan X. Langmuir, 2010, 26: 3615.
[57] Cui J, Zheng Y, Shen Z, Wan X. Langmuir, 2010, 26: 15508.
[58] Cui J, Shen Z, Wan X. Langmuir, 2010, 26: 97.
[59] Štěpánek P, Dukh M, Šaman D, Moravcová J, Knie?o L, Monti D, Venanzi M, Mancini G, Drašar P. Org. Biomol. Chem., 2007, 5: 960.
[60] Monti D, Venanzi M, Gatto E, Mancini G, Sorrenti A, Štěpánek P, Drašar P. New J. Chem., 2008, 32: 2127.
[61] Zheng J, Qiao W, Wan X, Gao J P, Wang Z Y. Chem. Mater., 2008, 20: 6163.
[62] Schmid S, Mena-Osteritz E, Kopyshev A, Bäuerle P. Org. Lett., 2009, 11: 5098.
[63] Pescitelli G, Omar O H, Operamolla A, Farinola G M, Bari L D. Macromolecules, 2012, 45: 9626.