Binding of secondary dialkylammonium salts by pyrido-21-crown-7

Pyrido-21-crown-7 (P21C7) has been synthesized and shown to form [2]pseudorotaxanes spontaneously with secondary dialkylammonium ions. These complexes are stronger than their benzo-21-crown-7 counterparts and much stronger than their dibenzo-24-crown-8 counterparts. Based on this new P21C7/secondary dialkylammonium salt recognition motif, a [2]rotaxane terminated by phenyl groups as stoppers has been successfully constructed using the threading-followed-by-stoppering technique. (c) 2008 Elsevier Ltd. All rights reserved.