Many industrial processes contribute significantly to environmental pollution due to widespread use of transition metal catalysts. One critical industrial process is ring-opening metathesis polymerization (ROMP), which is used to polymerize cyclic monomers. Due to the transition metal catalysts, this process contributes to environmental pollution. A recent study conducted by Dr. Boydston et al. has illuminated a new metal-free ROMP mechanism. While this is promising for moving toward more sustainable chemistry, further investigation is critical to optimize the process so that it is a viable alternative to the toxic ROMP process. This work investigates two potential monomers for usage with the metal-free ROMP mechanism to further illuminate the mechanics behind this novel process.<br/><br/>This project assesses potential intermediates in the MF-ROMP process using quantum chemical calculations to determine which are most viable for stereoselectivity. The ability to control the stereoselectivity is key to a polymerization mechanism, as it determines key aspects of the polymer such as the stability and melting point. Multiple aspects of the four isomers of dicyclopentadiene (DCPD) and dihydrodicyclopentadiene (DHDCPD) are assessed to determine what contributes to either the stabilization or destabilization of the resultant molecule bound with an anion. By varying steric (endo vs exo geometries) and electronic (saturated vs unsaturated bonds) features of the monomers, this work seeks to understand the stereoselective mechanism and provide guidance on how to best optimize this promising system. My poster will elucidate the results of my research and how the conformation of the monomer impacts the stereoselective capabilities.

Investigating the impact of anion pairing and isomerization on the energies of dicyclopentadiene and dihydrodicyclopentadiene

ACS Fall 2021

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