Highly tunable polyurethanes: organocatalyzed polyaddition and subsequent post-polymerization modification of pentafluorophenyl ester sidechains

A facile method for the synthesis of high molecular weight functionalized polyurethanes from a novel pentafluorophenyl ester-containing diol precursor is described. Specifically, polyurethanes containing the activated ester sidechains were synthesized via triflic acid-catalyzed polyaddition of the above diol with diisocyanates. This was followed by quantitative postpolymerization modification of the sidechains with various primary amines. This method represents an efficient and modular synthetic strategy for the preparation of functionalized polyurethanes.