Thioketones as a Simple Route Toward Thioester-Based Materials

For the first time, thioketones, as effective (thio)carbonyl compounds as a monomer in Passerini multicomponent polymerizations, are demonstrated. The resulting polymer is imbued with functional thioesters directly in the backbone. Additionally, the ease in using thioketone monomers (as opposed to thioaldehyde-based monomers) without the need for tedious workup and purification is highlighted. It is shown that soft matter materials made in this fashion can have their material properties easily tuned. Specifically, it is demonstrated that these polymers can be easily degraded via aminolysis, reduce their glass transition via dynamic trans-thioesterification, or transformed into thermoset materials with the addition of thiols and maleimides via thiol-ene chemistry.