While simple electronic parameters (e.g., HOMO level) positively correlated with monomer kp, steric parameters that described the overall size and shape of the monomer were more strongly correlated with kp. TCND-(CO2Me)2-which contains an electron-deficient cyclobutene-was discovered to be highly active towards DBU-catalyzed conjugate addition of dodecanethiol. This conjugate addition reaction was optimized on p(TCND-(CO2Me)2), and a variety of thiol nucleophiles were used to functionalize p(TCND-CO2Me)2) in this post-polymerization modification reaction.