Passerini addition polymerization of an AB-type monomer – A convenient route to versatile polyesters

An efficient way to synthesize an AB-type monomer, bearing a carboxylic acid and an aldehyde moiety, for Passerini step-growth polymerizations is described. This monomer was directly polymerized in a polyaddition approach applying the Passerini three-component reaction. Using various isocyanides for this polymerization resulted in polyesters with different amide side chains. Another structural feature of these polymers is a sulfur containing backbone, which is due to the monomer synthesis via thiol-ene chemistry. Oxidation of these polymers resulted in polysulfones exhibiting tunable thermal properties.