Recent Advances in the Synthesis of Ammonium-Based Rotaxanes 英文参考文献.docVIP

Molecules 2010, 15, 3709-3730; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Review Recent Advances in the Synthesis of Ammonium-Based Rotaxanes Dominic Thibeault and Jean-Fran?ois Morin * Département de Chimie, Centre de Recherche sur les Matériaux Avancés (CERMA), 1045 Ave. de la Médecine, Université Laval, Québec, G1V 0A6, Canada; E-Mail: dominic.thibeault@chm.ulaval.ca (D.T.) ? Author to whom correspondence should be addressed; E-Mail: jean-francois.morin@chm.ulaval.ca. Received: 1 April 2010; in revised form: 12 May 2010 / Accepted: 13 May 2010 / Published: 25 May 2010 Abstract: The number of synthetic methods enabling the preparation of ammonium-based rotaxanes has increased very rapidly in the past ten years. The challenge in the synthesis of rotaxanes results from the rather weak interactions between the ammonium-containing rod and the crown ether macrocycle in the pseudorotaxane structure that rely mostly on O·H hydrogen bonds. Indeed, no strong base or polar solvent that could break up H-bonding can be used during the formation of rotaxanes because the two components will separate as two distinct entities. Moreover, most of the reactions have to be performed at room temperature to favor the formation of pseudorotaxane in solution. These non-trivial prerequisites have been taken into account to develop efficient reaction conditions for the preparation of rotaxanes and those are described in detail along this review. Keywords: rotaxane; crown ether; synthesis; end-capping reaction; ring-closing reaction; functional rotaxane 1. Introduction The rotaxane architecture is considered as one of the most useful tools in the chemist’s toolbox to prepare functional synthetic nanomachines. The interest in these supramolecular architectures comes from their interlocked structure that provides them with high degree of freedom, thus allowing tunable translational motion at the nanosca