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.

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Publication Details

Journal
Macromolecular Rapid Communications
Published
2025-05-19
DOI
https://doi.org/10.1002/marc.202500076
Citations
2
Primary Topic
Polymer composites and self-healing
Type
article
Field-Weighted Citation Impact
1.21

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article

Thioketones as a Simple Route Toward Thioester‐Based Materials

Bryan T. Tuten, Hendrik Frisch, Anne D. Fernando Pulle
2 citations
Macromolecular Rapid Communications
Polymer composites and self-healing
1.21
article

Thioketones as a Simple Route Toward Thioester‐Based Materials

Bryan T. Tuten, Hendrik Frisch, Anne D. Fernando Pulle
article en
2 citations

Abstract

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.

Macromolecular Rapid CommunicationsVol. 46(14)
Queensland University of Technology (AU), The University of Texas at Tyler (US)
Australian Research Council
Openalex Percentile: Top 23%
Polymer composites and self-healing
1.21
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