Equilibrium ring opening metathesis polymerization (ROMP) of low strained cycloolefins is opportunistic for the development of novel materials capable of chemical recycling to monomer (CRM). The small enthalpic driving force (Δ<i>H</i><sub>p</sub>), or release of ring strain energy (RSE), of low strained monomers (RSE 5 kcal/mol) such as cyclopentenes creates an increased sensitivity to reaction conditions including temperature and concentration. While the low strain and ROMP sensitivity are typically viewed as an antagonist to polymerization, success affords new materials poised for effective depolymerization via ring closing metathesis (RCM). Therefore, these low RSE starting materials are ideal for chemical recycling to monomer and create a potential route towards a circular polymer economy. Furthermore, understanding RSE and other important energetics in the ROMP and CRM of low stained systems can help pinpoint promising new monomers and materials prior to laboratory execution. Density functional theory (DFT) can facilitate and accelerate experimental design and execution to fabricate novel materials by providing valuable insight into understudied systems such as cyclopentenes / polypentenamers. Accurate RSE predictions using DFT can infer the potential for a monomer to undergo CRM concomitant to necessary reaction conditions for leveraging equilibrium ROMP/RCM. Herein, the development of an easily implemented computational approach to screen a monomer’s potential for CRM will be discussed to reduce the time, cost, waste, and effort necessary to research new materials towards a more circular polymer economy.

DFT ring strain energy calculations of cyclopentene derivatives: Towards predictive design of chemically recyclable elastomers

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ACS Fall 2022

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