Acta Phys. -Chim. Sin. ›› 2010, Vol. 26 ›› Issue (07): 1811-1822.doi: 10.3866/PKU.WHXB20100722

• STRUCTURE CHEMISTRY • Previous Articles     Next Articles

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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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