中文 |
English |
Email Alert
基于脲基氢键组装的功能超分子凝胶
Functional Supramolecular Gels Self-Assembled by Hydrogen Bonding Among Urea-Based Gelators
有机小分子化合物在分子间氢键、π-π堆积、亲疏水作用、范德华力等非共价键弱相互作用力驱动下，自组装形成三维网络结构的物理凝胶称为超分子凝胶。含有脲基的凝胶因子由于其强氢键缔合能力以及与阴离子、金属离子、卤素化合物等作用的可调变多样性，成为组装超分子凝胶中特别有效的氢键组装单元。本文分别从单脲基、双脲基和多脲基的凝胶因子分类综述了基于脲基氢键组装的功能超分子凝胶的研究工作，特别是近几年来的重要进展。对一些成功例子，从分子设计及成胶操作条件控制等方面的精细调谐如何解决聚集-溶解这对主要矛盾，从而实现溶胶-凝胶的转化及其可能的应用前景进行了评述。本文展望了该领域的发展方向与趋势，指出超分子凝胶研究经过多年的快速发展，深化对其蕴含机制以及动力学过程的认识与调控以实现具有多种刺激响应、多重信号输出的多组分复合功能凝胶体系的加工制备是发展趋势与必然要求，展现出广泛的应用前景也极富挑战性。
Supramolecular gels with various ordered structures are constructed by the self-assembly of low-molecular-weight gelators (LMWGs) in some solvents driven by non-covalent interactions such as hydrogen bonding, π-π interactions, hydrophobic effects, and van der Waals interactions. Urea derivatives are among the most effective gelators for self-assembling supramolecular gels due to their strong hydrogen-bonding capability and various interactions and responsiveness to anion, metal cation and halide. In this paper, some representative research works especially the recent progress on functional supramolecular gels constructed from urea-based gelators are reviewed according to mono-, bis-and multi-urea systems. Furthermore, brief comments are made on their reversible sol-gel transformation and possible applications for some typical cases from the viewpoint of finely tuning the dissolution-aggregation balance mainly based on molecular design of gelators and the optimization of their gelation conditions. Finally,the research trends and application perspectives of supramolecular gels are concisely expected and point out that after many years rapid development in this field, the clear understanding of gelation kinetics and the mechanism involved are the imperative and challenging work, and multi-component supramolecular gels with complex internal structures and controllable physical properties showing fast response to variant external stimuli may constitute the new generation of functional gels.
Contents
1 Introduction to supramolecular gels
2 Mono-urea functional supramolecular gels
3 Bis-urea functional supramolecular gels
3.1 Bis-urea gels with aliphatic spacer
3.2 Bis-urea gels with aromatic spacer
4 Multi-urea functional supramolecular gels
5 Conclusions and outlook
超分子凝胶
supramolecular gels
[1] Flory P J. Faraday Discuss, 1974, 57: 7.
[2] Terech P, Weiss R G. Chem. Rev., 1997, 97: 3133.
[3] Abdallah D J, Weiss R G. Adv. Mater., 2000, 12: 1237.
[4] Fages F, Vögtle F, ?ini D? M. Top. Curr. Chem., 2005, 256: 77.
[5] Estroff L A, Hamilton A D. Chem. Rev., 2004, 104: 1201.
[6] Sangeetha N M, Maitra U. Chem. Soc. Rev., 2005, 34: 821.
[7] George M, Weiss R G. Acc. Chem. Res., 2006, 39: 489.
[8] Dastidar P. Chem. Soc. Rev., 2008, 37: 2699.
[9] Smith D K. Chem. Soc. Rev., 2009, 38: 684.
[10] Piepenbrock M M, Lloyd G O, Clarke N, Steed J W. Chem. Rev., 2010, 110: 1960.
[11] Buerkle L E, Rowan S. J. Chem. Soc. Rev., 2012, 41: 6089.
[12] Tomasini C, Castellucci N. Chem. Soc. Rev., 2013, 42: 156.
[13] Hirst A R, Escuder B, Miravet J F, Smith D K. Angew. Chem. Int. Ed., 2008, 47: 8002.
[14] Wang X, Horri A, Zhang S. Soft Matter, 2008, 4: 2388.
[15] Stupp S I. Nano Lett., 2010, 10: 4783.
[16] Silva G A, Czeisler C, Niece K L, Beniash E, Harrington D A, Kessler J A, Stupp S I. Science, 2004, 303: 1352.
[17] Yagai S, Nakajima T, Kishikawa K, Kohmoto S, Karatsu T, Kitamura A. J. Am. Chem. Soc., 2005, 127: 11134.
[18] de Jong J J D, Lucas L N, Kellogg R M, van Esch J H, Feringa B L. Science, 2004, 304: 278.
[19] Mukhopadhyay P, Iwashita Y, Shirakawa M, Kawano S, Fujita N, Shinkai S. Angew. Chem. Int. Ed., 2006, 45: 1592.
[20] Kato T, Yasuda T, Kamikawa Y, Yoshio M. Chem. Commun., 2009: 729.
[21] Kato T, Hirai Y, Nakaso S, Moriyama M, Chem. Soc. Rev., 2007, 36: 1857.
[22] Yagai S, Kubota S, Iwashima T, Kishikawa K, Nakanishi T, Karatsu T, Kitamura A. Chem. Eur. J., 2008, 14: 5246.
[23] Kitamura T, Nakaso S, Mizoshita N, Tochigi Y, Shimomura T, Moriyama M, Ito K, Kato T. J. Am. Chem. Soc., 2005, 127: 14769.
[24] Segarra-Maset M D, Nebot V J, Miravet J F, Escuder B. Chem. Sov. Rev., 2013, 42: 7086.
[25] Yang X Y, Zhang G X, Zhang D Q. J. Mater. Chem., 2012, 22: 38.
[26] 孔丽(Kong L), 孙涛(Sun T), 张峰(Zhang F), 辛飞飞(Xin F F), 郝爱友(Hao A Y). 化学进展(Progress in Chemistry), 2012, 24(5): 790.
[27] 王毓江(Wang Y J), 唐黎明(Tang L M), 于建(Yu J). 化学进展(Progress in Chemistry), 2009, 21(6): 1312.
[28] 周义锋(Zhou Y F). 化学进展(Progress in Chemistry), 2011, 23(1): 125.
[29] 沈利英(Shen L Y), 陈肖卓(Chen X Z), 于海涛(Yu H T), 梁刚(Liang G). 有机化学(Chinese Journal of Organic Chemistry), 2009, 29(3): 321.
[30] Steed J W. Chem. Sov. Rev., 2010, 39: 3686.
[31] Lloyd G O, Steed J W. Nature Chem., 2009, 1: 437.
[32] Foster J A, Piepenbrock M M, Lloyd G O, Clarke N, Howard J A K, Steed J W. Nature Chem., 2010, 2: 1037.
[33] George M, Tan G, John V T, Weiss R G. Chem. Eur. J., 2005, 11: 3243.
[34] Rodrguez-Llansola F, Escuder B, Miravet J F, Hermida-Merino D, Hamley I W, Cardin C J, Hayes W. Chem. Commun., 2010, 46: 7960.
[35] Ghosh K, Kar D. Org. Biomol. Chem., 2012, 10: 8800.
[36] Wang G, Hamilton A D. Chem. Commun., 2003: 310.
[37] Patra T, Pal A, Dey J. J. Colloid Interface Sci., 2010, 344: 10.
[38] Pal A, Dey J. Langmuir, 2011, 27: 3401.
[39] Pal A, Dey J. Langmuir, 2013, 29: 2120.
[40] Wang C, Zhang D Q, Xiang J F, Zhu D B. Langmuir, 2007, 23: 9195.
[41] Hwang I, Jeon W S, Kim H J, Kim D, Kim H, Selvapalam N, Fujita N, Shinkai S, Kim K. Angew. Chem. Int. Ed., 2007, 46: 210.
[42] Tsuge A, Matsushita R, Sakura K, Moriguchi T, Araki K. Chem. Lett., 2012, 41: 485.
[43] Mutoh K, Abe J. Chem. Commun., 2011, 47: 8868.
[44] Hsueh S Y, Kuo C T, Lu T W, Lai C C, Liu Y H, Hsu H F, Peng S M, Chen C H, Chiu S H. Angew. Chem. Int. Ed., 2010, 49: 9170.
[45] Kida T, Marui Y, Miyawaki K, Kato T, Akashi M. Chem. Commun., 2009, 3889.
[46] Jung J H, Kobayashi H, Masuda M, Shimizu T, Shinkai S. J. Am. Chem. Soc., 2001, 123: 8785.
[47] van der L S, Feringa B L, Kellogg R M, van Esch. J H. Langmuir, 2002, 18: 7136.
[48] Adarsh N N, Kumar D K, Dastidar P. Tetrahedron, 2007, 63: 7386.
[49] Arai S, Imazu K, Kusuda S, Yoshihama I, Tonegawa M, Nishimura Y, Kitahara K, Oishi S, Takemura T. Chem. Lett., 2006, 35: 634.
[50] Braga D, d'Agostino S, D'Amen E, Grepioni F. Chem. Commun., 2011, 47: 5154.
[51] van Esch J, Feyter S D, Kellogg R M, Schryver F D, Feringa B L S. Chem. Eur. J., 1997, 3: 1238.
[52] van Esch J, Kellogg R M, Feringa B L. Tetrahedron Lett., 1997, 38: 281.
[53] Piepenbrock M O M, Lloyd G O, Clarke N, Steed J W. Chem. Commun., 2008, 2644.
[54] Lloyd G O, Piepenbrock M O M, Foster J A, Clarke N, Steed J W. Soft Matter, 2012, 8: 204.
[55] Yagai S, Kubota S, Iwashima T, Kishikawa K, Nakanishi T, Karatsu T, Kitamura A. Chem. Eur. J., 2008, 14: 5246.
[56] Coates I A, Smith D K. Chem. Eur. J., 2009, 15: 6340.
[57] Edwards W, Lagadec C A, Smith D K. Soft Matter, 2011, 7: 110.
[58] Hardy J G, Hirst A R, Ashworth I, Brennan C, Smith D K. Tetrahedron, 2007, 63: 7397.
[59] Rubio J, Martí-Centelles V, Burguete M I, Luis S V. Tetrahedron, 2013, 69: 2302.
[60] van Esch J, Schoonbeek F, de Loos M, Kooijman H, Spek A L, Kellogg R M, Feringa B L. Chem. Eur. J., 1999, 5: 937.
[61] de Loos M, van Esch J, Stokroos I, Kellogg R M, Feringa B L. J. Am. Chem. Soc., 1997, 119: 12675.
[62] Brinksma J, Feringa B L, Kellogg R M, Vreeker R, van Esch J. Langmuir, 2000, 16: 9249.
[63] de Loos M, van Esch J, Kellogg R M, Feringa B L. Angew. Chem. Int. Ed., 2001, 40: 613.
[64] Carr A J, Melendez R, Geib S J, Hamilton A D. Tetrahedron Lett., 1998, 39: 7447.
[65] Yabuuchi K, Emmanuel M O, Kato T. Org. Biomol. Chem., 2003, 1: 3464.
[66] Yang H, Yi T, Zhou Z G, Zhou Y F, Wu J, Xu M, Li F Y, Huang C H. Langmuir, 2007, 23: 8224.
[67] Zhang C, Wang J, Wang J J, Li M, Yang X L, Xu H B. Chem. Eur. J., 2012, 18: 14954.
[68] Qi Z, de Molina P M, Jiang W, Wang Q, Nowosinski K, Schulz A, Gradzielski M, Schalley C A. Chem. Sci., 2012, 3: 2073.
[69] Das A, Ghosh S. Chem. Eur. J., 2010, 16: 13622.
[70] Schoonbeek F S, van Esch J H, Wegewijs B. Angew. Chem. Int. Ed., 1999, 38: 1393.
[71] Akazawa M, Uchida K, de Jong J J D, Areephong J, Stuart M, Caroli G, Browne W R, Feringa B L. Org. Biomol. Chem., 2008, 6: 1544.
[72] Miravet J F, Escuder B. Org. Lett., 2005, 7: 4791.
[73] Dou C D, Wang C G, Zhang H Y, Gao H Z, Wang Y. Chem. Eur. J., 2010, 16: 10744.
[74] Piepenbrock, M O M, Clarke N, Steed J W. Langmuir, 2009, 25(15): 8451.
[75] Piepenbrock, M O M, Clarke N, Steed J W. Soft Matter, 2010, 6: 3541.
[76] Piepenbrock, M O M, Clarke N, Steed J W. Soft Matter, 2011, 7: 2412.
[77] Meazza L, Foster J A, Fucke K, Metrangolo P, Resnati G, Steed J W. Nature Chem., 2013, 5: 42.
[78] Yamanaka M. J. Incl. Phenom. Macrocycl. Chem., 2013, 77: 33.
[79] de Loos M, Ligtenbarg, A G J, van Esch J, Kooijman H, Spek A L, Hage R, Kellogg R M, Feringa B L. Eur. J. Org. Chem., 2000, 3675.
[80] Stanley C E, Clarke N, Anderson K M, Elder J A, Lenthall J T, Steed J W. Chem. Commun., 2006, 3199.
[81] Zhou Y F, Yi T, Li T C, Zhou Z G, Li F Y, Huang W, Huang C H. Chem. Mater., 2006, 18: 2974.
[82] Deng C, Fang R, Guan Y F, Jiang J L, Lin L, Wang L Y. Chem. Commun., 2012, 48: 7973.
[83] de Loos M, van Esch J H, Kellogg R M, Feringa B L. Tetrahedron., 2007, 63: 7285.
[84] Yamanaka M, Nakamura T, Nakagawa T, Itagaki H. Tetrahedron Lett., 2007, 48: 8990.
[85] Aoyama R, Amakatsu M, Yamanaka M. Supramol. Chem., 2011, 23: 140.
[86] Yamamichi S, Jinno Y, Haraya N, Oyoshi T, Tomitori H, Kashiwagi K, Yamanaka M. Chem. Commun., 2011, 47: 10344.
[87] Jinno Y, Yamanaka M. Chem. Asian J., 2012, 7: 1768.
[88] Yamanaka M, Haraya N, Yamamichi S. Chem. Asian J., 2011, 6: 1022.
[89] Tamaru S, Uchino S, Takeuchi M, Ikeda M, Hatano T, Shinkai S. Tetrahedron Lett., 2002, 43: 3751.
[90] Kishida T, Fujita N, Sada K, Shinkai S. Langmuir, 2005, 21: 9432.
[91] Lu C C, Su S K. Supramol. Chem., 2009, 21: 557.
[92] Ladet S, David L, Domard A. Nature, 2008, 452: 76.
[93] Elisseeff J. Nature Mater., 2008, 7: 271.
/
| 〈 |
|
〉 |
PDF
(8414KB)
