物理化学学报 >> 2010, Vol. 26 >> Issue (07): 1811-1822.doi: 10.3866/PKU.WHXB20100722

结构化学 上一篇    下一篇

芳酰胺类大环一步高效合成及其成环机理研究进展

胡晋川, 冯文, 李向晖, 杨柳青, 袁立华, 何兰, 龚兵   

  1. 四川大学化学学院, 教育部辐射物理与技术重点实验室, 原子核科学技术研究所, 成都 610064
    Department of Chemistry, University at Buffalo, The State University of New York at Buffalo, Buffalo, New York 14260, USA
    北京师范大学化学学院, 北京 100875
  • 收稿日期:2010-01-26 修回日期:2010-04-30 发布日期:2010-07-02
  • 通讯作者: 袁立华, 何兰 E-mail:lhyuan@scu.edu.cn; helan1961@yahoo.com.cn

One-Pot Formation of Aromatic Oligoamide Macrocycles and the Corresponding Mechanism

HU Jin-Chuan, FENG Wen, LI Xiang-Hui, YANG Liu-Qing, YUAN Li-Hua, HE Lan, GONG Bing   

  1. Institute of Nuclear Science and Technology, Key Laboratory for Radiation Physics and Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China
    Department of Chemistry, University at Buffalo, The State University of New York at Buffalo, Buffalo, New York 14260, USA
    College of Chemistry, Beijing Normal University, Beijing 100875, P. R. China
  • Received:2010-01-26 Revised:2010-04-30 Published:2010-07-02
  • Contact: YUAN Li-Hua, HE Lan E-mail:lhyuan@scu.edu.cn; helan1961@yahoo.com.cn

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摘要：

总结了最近发现的新型芳酰胺及芳酰肼大环一步合成反应, 着重探讨了由分子内三中心氢键所引导的高效一步成环反应机理. 这类反应是由未成环寡聚物前体的折叠构象所构筑, 不仅高效, 而且反应机理新颖, 提供了传统成环反应难以得到的几类刚性大环的合成方法. 这些大环化合物表现出对客体识别的高度专一性, 并能形成具有高通量性的跨膜孔道.

关键词: 一步成环反应, 机理, 氢键, 刚性大环

Abstract:

In this review, we summarize a newly discovered one-pot process for the synthesis of aromatic oligoamide and oligohydrazide macrocycles. A mechanism for these highly efficient one-pot macrocyclization reactions is presented and discussed. The unprecedented high efficiencies of these one-pot macrocyclization reactions are rationalized based on the folding of uncyclized oligomeric precursors, which is enforced by intramolecular hydrogen bonds. These one-pot macrocyclization reactions, with their unusually high efficiencies and novel mechanism, afford several new classes of shape-persistent macrocycles that are otherwise difficult to obtain using traditional methods. It has been already demonstrated that these macrocycles possess unique properties in the specific recognition of guest species and the formation of highly conducting transmembrane pores.

Key words: One-pot macrocyclization, Mechanism, Hydrogen bond, Shape-persistent macrocycle