Fused-polynorbornane frameworks: optimising the synthesis and “Edge” assembly

Polynorbornanes frameworks are highly preorganised, rigid and stable aliphatic scaffolds. These frameworks can be functionalised with a variety of functional groups and have displayed effective uses in host-guest chemistry (e.g. anion recognition). Research to date has almost entirely focused on “end” and “centre” functionalisation of the [n]polynorbornane framework with little research completed in exploring the “edge” of the [n]polynorbornane framework.
The [n]polynorbornane frameworks have also been used in the construction of metallosupramolecular assemblies. A metallosupramolecular assembly is a continuous network made from the interactions of organic ligands with metal centres. These assemblies can have a range of geometries and unique useful properties (e.g. porosity for gas capture and storage).
In this project, a [3]polynorbornane framework was constructed with the aim of exploring “edge” functionalisation. The entire synthetic process was optimised and all compounds characterised using 1H NMR spectroscopy. Furthermore, for taking advantage of the “edge” of polynorbornane frameworks a metallosupramolecular assembly was devised using zinc and an epoxide diacid.
The outcome of this project was a reliable synthetic process for creating [3]polynorbornane frameworks (using both microwave and traditional heating methodology) and an approach for exploiting the “edge” of [n]polynorbornane frameworks with respect to assembling metallosupramolecular architectures.