Assembly of Carbon Cages via Alkene Metathesis and their Potential Applications

In recent years, porous materials have gained great interest not only for their structural elegance, but also for their diverse applications. Discrete molecules including macrocycles and macromolecular cages are included in these porous materials. Leveraging dynamic covalent chemistry (DCvC), three-dimensional molecular cages can be utilized in clean energy for molecular separation and in the biomedical field for discovery of new methods through binding/encapsulating other molecules. DCvC has been explored for the synthesis of organic cage compounds through a variety of synthetic tools including imine condensation, boronic ester condensation and alkene metathesis. The aim of our project is to develop an efficient synthetic method to construct a rigid three-dimensional organic dodecahedral cage utilizing dynamic covalent chemistry (DCvC). In our efforts to develop a new route toward polyhedral cage synthesis, we envision a utilization of tritopic alkene monomers exposed to alkene metathesis conditions. This thesis describes the exploration of various synthetic routes to optimize the synthesis of the tritopic alkene monomer. Though initial cage synthesis trials have been challenging, our work thus far has highlighted the importance of maintaining the solubility of monomer and oligomer intermediates during cage assembly