3), and TCND-CO2Me reached only 3% conversion (Table , entry 4). These results correlate with the DFT calculated LUMO energies (M06-2X/def-TZVP) for each molecule (Table ), suggesting that the rigid structure of TCND-(CO2Me)2 paired with its two electron-withdrawing ester substituents make it a better electrophile for conjugate addition. Meanwhile, as discussed above, these structural features are also key for (1) ensuring a high ROMP kp (by avoiding steric hindrance associated with diesters appended directly to the exo-NB) and ( ) avoiding undesired cross-linking during ROMP (as observed for TCND-CO2Me), making TCND-(CO2Me)2 a particularly promising monomer for further exploration. Conditions: p(TCND-(CO2Me)2) in DMF (50 mg/mL) at room temperature. Dodecanethiol was added, followed by the addition of DBU as a stock solution in DMF (1:9 v:v DBU:DMF) and was allowed to react for 1 hour. a Conversion was assessed by comparing the integration of the backbone olefinic protons (4.8 ppm -5.7 ppm) versus the integration of the terminal -CH3 of the dodecanethiol side-chain (0.9 ppm).