The construction of catenanes, comprised of between two and seven interlocked rings, has been achieved. Two tris-1,5-naphtho-57-crown-15 macrocycles template the formation of cyclobis(paraquat-4,4'-biphenylene) to give a catenane, which acts as a template for the construction of one and then another cyclobis(paraquat-p-phenylene) to give a - and catenane (Olympiadane). When high pressure was used in these templated syntheses, a - and catenane, as well as a catenane that is topologically isomeric with Olympiadane, were also obtained. X-ray analyses of the -, -, and catenanes reveal an optimum use of electrostatic, π-π stacking, [C- H···π] interactions, and [C-H···O] hydrogen bonds in the organization of the component rings within the molecules. Noteworthy in the catenane structure is the location of four of the PF6/- anions within voids present in the 20+ ion. Temperature-dependent 1H NMR spectroscopic studies and electrochemical investigations have revealed the dynamic and redox behavior of these catenanes in solution.
ASJC Scopus subject areas
- Colloid and Surface Chemistry