Toward interlocked molecules beyond catenanes and rotaxanes

Abstract

A linear bis secondary dialkylammonium ion-containing scaffold - based upon an anthracenyl core-has been synthesized. It has been demonstrated that it is possible to dock either one or two dibenzo[24]crown-8 (DB24C8) macrocycles onto this scaffold to afford either a [2]-or [3]pseudorotaxane, respectively. In solution, the association constants for the formation of each of these species has been quantified by employing 1H NMR spectroscopy, and both species survive in the "gas phase" as evidenced by FAB mass spectrometry. Additionally, the X-ray crystal superstructure of the [3]pseudorotaxane has been determined.