Clippane: A Mechanically Interlocked Molecule (MIM) Based on Molecular Tweezers

Abstract

In this study we report the preparation of a new mechanically interlocked molecule formed by the self-aggregation of two metallotweezers composed by two pyrene-imidazolylidene gold(I) arms and a pyridine-centered pentacyclic bis-alkynyl linker. The mechanically interlocked nature of this molecule arises from the presence of the bulky tert-butyl groups attached to the sides of the pyrene moieties of the arms of the tweezer, which act as stoppers avoiding the dissociation of the self-aggregated metallotweezer dimer once it is formed. By combining experimental techniques, we were able to confirm the mechanically interlocked nature of this molecule in solution, in the gas phase and in the solid state. The behavior of the tert-butyl substituted tweezer differs greatly form that shown by the tweezer lacking of these bulky groups, whose dimeric structure is in equilibrium with the monomeric structure, therefore not showing any mechanical coercion that avoids the disassembly of the self-aggregated structure.