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化学进展 2011, Vol. 23 Issue (01): 1-12   后一篇

• Mini Accounts •

氢键介质的芳酰胺折叠体：从构象控制到功能演化

黎占亭1,2   

  1. 1. 复旦大学化学系 上海 200433,China;
    2. 中国科学院上海有机化学研究所 上海 200032,China
  • 出版日期:2011-01-20 发布日期:2011-09-02
  • 作者简介:Zhan-Ting Li was born in 1966 in Shangcai, Henan Province. He received his BSc degree in 1985 from Zhengzhou University and his Ph.D. degree in fluorine chemistry in 1992 with Professor Qing- Yun Chen at Shanghai Institute of Organic Chemistry (SIOC). He did a postdoctoral research with Professor Jan Becher at the University of South Denmark (formerly Odense University) (1994–1995) and was a visiting scholar with Professor Steven C. Zimmerman at The University of Illinois at Urbana- Champaign (2000–2001). He was promoted to full professor at SIOC in 2003 and joined the Chemistry De partmentfaculty, Fudan University in 2010. His researches are mainly concerned with the hydrogen bonding-related bimimetic structures, molecular recognition and self-assembly, conjugated structures and fluorine–containing materials.
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Hydrogen bonded arylamide foldamers: From conformational control to functional evolution

Li Zhan ting1,2   

  1. 1. Department of Chemistry, Fudan University, 220 Handan Road, Shanghai 200433, China;
    2. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China
  • Online:2011-01-20 Published:2011-09-02

根据芳环上酰胺和氢键受体位置的不同，氢键介质的芳酰胺和酰肼折叠体可以产生折叠、螺旋、“ 之” 字型、直线型及其它扩展型的构象。由于氢键具有较高的稳定性及芳酰胺固有的平面性特征，这一系列的芳酰胺寡聚体拥有较高的可预测的构象。芳酰胺骨架本身可以通过简单的酰胺键偶合反应构筑，而不同的官能团也可以选择性地引入到特定的骨架内部或其侧链内。因此，在过去几年内，我们重点研究了它们在构筑新的分子镊，形成凝胶、囊泡和液晶等有序功能超分子体系及促进大环分子体系合成方面的应用。近期我们又发现，氢键驱动的折叠片段能够并入到聚合物中，通过分子内氢键的断裂和恢复可逆调控聚合物的力学性质。本文主要介绍我们实验室在氢键驱动的芳酰胺折叠体结构– 性质关系研究方面取得的进展。

关键词： 氢键, 折叠体, 芳酰胺, 超分子化学, 寡聚体, 大分子, 预组织

Hydrogen bonded aryl amide and hydrazide foldamers may adopt folded or helical, zigzag, straight or other extended conformations, depending on the positions of the amides and hydrogen bonding acceptors on the aromatic rings. Because of the relatively high strength of hydrogen bonding and the intrinsic planarity of the arylamide units, this family of amide oligomers usually possesses highly predictable conformations. The frameworks themselves can be conveniently constructed via simple amide coupling reactions, while discrete functional groups can be introduced to the frameworks or appended side chains at required positions. Thus, in the past few years, we have focused on their applications in designing new molecular tweezers, for generating welldefined and functional supramolecular systems, including organogels, vesicles and liquid crystals, and for directing the formation of complicated macrocyclic systems. More recently, we have found that hydrogen bonding-driven folded segments can also be incorporated into polymers to reversibly tune their mechanical property through the breaking and recovering of the intramolecular hydrogen bonds. This Mini Account summarizes our recent efforts along this line.

Key words: hydrogen bonding, foldamer, aromatic amide, supramolecular chemistry, oligomer, macromolecule, preorganization
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