English
新闻公告
More
化学进展 2015, Vol. 27 Issue (6): 675-686 DOI: 10.7536/PC150129 前一篇   后一篇

• 超分子化学专辑 •

模板导向的亚胺型夹套法在构筑N-杂冠醚类机械互锁分子中的应用

韩勰, 胡芳, 葛豪杰, 刘盛华, 尹军*   

  1. 华中师范大学化学学院 农药与化学生物学教育部重点实验室 武汉 430079
  • 收稿日期:2015-01-01 修回日期:2015-02-01 出版日期:2015-06-15 发布日期:2015-03-16
  • 通讯作者: 尹军 E-mail:yinj@mail.ccnu.edu.cn
  • 基金资助:
    国家自然科学基金项目(No.21472059,21402057)资助

The Application of Templated-Directed Clipping Approach in Constructing Mechanically Interlocked Molecules Based on N-Hetero Crown Ethers

Han Xie, Hu Fang, Ge Haojie, Liu Shenghua, Yin Jun*   

  1. Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, China
  • Received:2015-01-01 Revised:2015-02-01 Online:2015-06-15 Published:2015-03-16
  • Contact: 10.7536/PC150129 E-mail:yinj@mail.ccnu.edu.cn
  • Supported by:
    The work was supported by the National Natural Science Foundation of China (No. 21472059, 21402057).
近些年来,随着超分子化学的发展,基于N-杂冠醚骨架的机械互锁分子受到了人们越来越多的关注。与传统的合成方法相比较,基于模板导向的亚胺型夹套法在构建N-杂冠醚类机械互锁分子中具有独特的优势,并且取得了许多重要的进展。科学家们不仅拓展了基于N-杂冠醚的机械互锁分子的拓扑学结构,而且丰富了其在多个领域的应用。基于此,本文总结了近十年来模板导向的亚胺型夹套法在构筑具有不同拓扑学结构的N-杂冠醚类机械互锁分子(如轮烷、索烃、杂轮烷、轮烷-索烃集成体、低聚物、菊花链和树枝状分子)及其在功能化方面的应用进展。
With the rapid development of supramolecular chemistry, the mechanically interlocked molecules based on N-hetero crown ethers (NHCE) have attracted increasing interest in recent years. Compared with the traditional synthetic methods, the templated clipping approach has unique advantages in constructing mechanically interlocked molecules based on NHCE, and many important advances have been obtained. Scientists have not only gradually expanded the topological structures of mechanically interlocked molecules based on NHCE, but also enriched their application in various regions. Herein, we summarize the progress of templated clipping approach in the structure construction of the mechanically interlocked molecules (such as rotaxanes, catenanes, heterorotaxanes, rotacatenanes, oligomers, daisy chains and dendritic molecules) and their potential applications.

Contents
1 Introduction
2 Rotaxanes based on NHCE
2.1 Oligorotaxanes
2.2 Rectangular rotaxanes
2.3 Dendritic rotaxanes
2.4 Heterorotaxanes
2.5 Functional rotaxanes
3 Catenanes based on NHCE
4 Rotaxane-fused-catenane integrations
5 Daisy chains based on NHCE
6 Conclusion

中图分类号: 

()
[1] Stoddart J F. Chem. Soc. Rev., 2009, 38: 1802.
[2] Mateo-Alonso A. Chem. Commun., 2010, 46: 9089.
[3] Fang L, Olson M A, Benítez D, Tkatchouk E, Goddard W A, Stoddart J F. Chem. Soc. Rev., 2010, 39: 17.
[4] Boyle M M, Smaldone R A, Whalley A C, Ambrogio M W, Botros Y Y, Stoddart J F. Chem. Sci., 2011, 2: 204.
[5] Ramakrishnam Raju M V, Lin H C. Org. Lett., 2014, 16: 5564.
[6] 陈传峰(Chen C F), 杨勇(Yang Y). 超分子组装: 结构与功能(Supramolecular Assembly : Structure and Function). 北京: 科学出版社(Beijing: Science Press), 2014.
[7] 孙书(Sun S), 石建兵(Shi J B), 董宇平(Dong Y P), 胡晓玉(Hu X Y), 王乐勇(Wang L Y). 化学进展(Progress in Chemistry), 2014, 26(8): 1409
[8] 杨再文(Yang Z W), 刘向荣(Liu X R), 赵顺省(Zhao S S), 何金梅(He J M). 化学进展(Progress in Chemistry), 2014, 26(12): 1899.
[9] Cheng Y, Liu Y. Chem. Soc. Rev., 2010, 39: 495.
[10] Ma X, Tian H. Chem. Soc. Rev., 2010, 39: 70.
[11] Hänni K D, Leigh D A. Chem. Soc. Rev., 2010, 39: 1240.
[12] Beves J E, Blight B A, Campbell C J, Leigh D A, McBurney R T. Angew. Chem. Int. Ed., 2011, 50: 9260.
[13] Qu D H, Tian H. Chem. Sci., 2011, 2: 1011.
[14] Neal E A, Goldup S M. Chem. Commun., 2014, 50: 5128.
[15] Dong S Y, Zheng B, Wang F, Huang F H. Acc. Chem. Res., 2014, 47: 1982.
[16] 刘鹏(Liu P), 邵学广(Shao X G), 蔡文生(Cai W S). 化学进展(Progress in Chemistry), 2013, 25(5): 692.
[17] Yang Y W, Sun Y L, Song N. Acc. Chem. Res., 2014, 47: 1950.
[18] Han Y, Meng Z, Ma Y X, Chen C F. Acc. Chem. Res., 2014, 47: 2026.
[19] Coskun A, Spruell J M, Barin G, Dichtel W R, Flood A H, Botros Y Y, Stoddart J F. Chem. Soc. Rev., 2012, 41: 4827.
[20] 刘育(Liu Y), 尤长城(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 Acceptors). 天津: 南开大学出版社(Tianjin: Nankai University Press), 2001.
[21] 刘育(Liu Y), 张衡益(Zhang H Y), 李莉(Li L), 王浩(Wang H). 纳米超分子化学——从合成受体到功能组装体(Nanoscale Supramolecular Chemistry——From Synthetic Receptors to Functional Assemblies). 北京: 化学工业出版社(Beijing: Chemical Industry Press), 2004.
[22] 黄飞鹤(Huang F H), 翟春熙(Zhai C X), 郑波(Zheng B),李世军(Li S J). 超分子聚合物(Supralmolecular Polymers). 杭州: 浙江大学出版社(Hangzhou: Zhejiang University Press), 2012.
[23] Steed J W, Atwood J L. Supramolecular Chemistry, 2nd edition, Wiley, New York: 2009.
[24] Glink P T, Oliva A I, Stoddart J F, White A J P, Williams D J. Angew. Chem. Int. Ed., 2001, 40: 1870.
[25] Leung K C, Wong W Y, Aricó F, Haussmann P C, Stoddart J F. Org. Biomol. Chem., 2010, 8: 83.
[26] Frisch H L, Wasserman E. J. Am. Chem. Soc., 1961, 83: 3789.
[27] Kay E R, Leigh D A, Zerbetto F. Angew. Chem. Int. Ed., 2007, 46: 72.
[28] Wu J S, Leung K C F, Stoddart J F. Proc. Natl. Acad. Sci. U. S. A., 2007, 104: 17266.
[29] Yin J, Dasgupta S, Wu J S. Org. Lett., 2010, 12: 1712.
[30] Belowich M E, Valente C, Stoddart J F. Angew. Chem. Int. Ed., 2010, 49: 7208.
[31] Belowich M E, Valente C, Smaldone R A, Friedman D C, Thiel J, Cronin L, Stoddart J F. J. Am. Chem. Soc., 2012, 134: 5243.
[32] Aricó F, Chang T, Cantrill S J, Khan S I, Stoddart J F. Chem. Eur. J., 2005, 11: 4655.
[33] Astruc D, Chardac F. Chem. Rev., 2001, 101: 2991.
[34] Rosen B M, Wilson C J, Wilson D A, Peterca M, Imam M R, Percec V. Chem. Rev., 2009, 109: 6275.
[35] Leung K C, Aricó F, Chang T, Cantrill S J, Stoddart J F. J. Am. Chem. Soc., 2005, 127: 5808
[36] Leung K C, Aricó F, Chang T, Cantrill S J, Stoddart J F. Macromolecules, 2007, 40: 3951.
[37] Liu G X, Li Z Y, Wu D, Xue W, Li T T, Liu S H, Yin J. J. Org. Chem., 2014, 79: 643.
[38] Yin J, Chi C Y, Wu J S. Org. Biomol. Chem., 2010, 8: 2594.
[39] Wilson E A, Vermeulen N A, McGonigal P R, Avestro A J, Sarjeant A A, Stern C L, Stoddart J F. Chem. Commun., 2014, 50: 9665.
[40] Li Z Y, Liu G X, Xue W, Wu D, Yang Y W, Wu J S, Liu S H, Yoon J Y, Yin J. J. Org. Chem., 2013, 78: 11560.
[41] Zhou W D, Li J B, He X R, Li C H, Lv J, Li Y L, Wang S, Liu H B, Zhu D B. Chem. Eur. J., 2008, 14: 754.
[42] Avestro A J, Gardner D M, Vermeulen N A, Wilson E A, Schneebeli S T, Whalley A C, Belowich M E, Carmieli R, Wasielewski M R, Stoddart J F. Angew. Chem. Int. Ed., 2014, 53: 4442.
[43] Hu F, Huang J Y, Cao M J, Chen Z, Yang Y W, Liu S H, Yin J. Org. Biomol. Chem., 2014, 12: 7712.
[44] Sauvage J P, Collin J P, Chambron, J C, Gulllerez S, Coudret C. Chem. Rev., 1994, 94: 993
[45] Stoddart J F. Chem. Soc. Rev., 2009, 38: 1521.
[46] Li Z Y, Liu W J, Wu J S, Liu S H, Yin J. J. Org. Chem., 2012, 77: 7129.
[47] Li Z Y, Hu F, Liu G X, Xue W, Chen X Q, Liu S H, Yin J. Org. Biomol. Chem., 2014, 12: 7702.
[48] Xue W, Li Z Y, Liu G X, Chen X Q, Li T T, Liu S H, Yin J. Org. Biomol. Chem., 2014, 12: 4862.
[49] Bozdemir O A, Barin G, Belowich M E, Basuray A N, Beuerle F, Stoddart J F. Chem. Commun., 2012, 48: 10401.
[1] 汪含笑, 韩莹, 陈传峰*. 基于三维不对称主体的客体方向选择性穿线作用及其组装体的构建[J]. 化学进展, 2018, 30(5): 616-627.