The self-assembly and dynamic properties of thiophene-containing [2]catenanes

Abstract

The template-directed syntheses of two novel [2]catenanes, incorporating bisparaphenylene-34-crown-10 interlocked with tetracationic cyclophanes, containing either one or two 2,5-disubstituted thiophene residues in addition to two bipyridinium units, are reported. The X-ray crystal structures of one of these [2]catenanes and of its component tetracationic cyclophane are reported. The former exhibits short [S···O] contacts in addition to the expected π-π and [C-H···O] stabilising interactions. Dynamic 1H NMR spectroscopy has revealed that there is a substantial degree of order which characterises the molecular structures of both these [2]catenanes in solution at a noncovalent bonding level. Identifying and understanding these noncovalent bonding interactions between the molecular components are crucial to the design of catenanes that will self-assemble in a highly efficient manner.