Thiol-Ene Networks from Sequence-Defined Polyurethane Macromers

Emily A. Hoff, Guilhem X. De Hoe, Christopher M. Mulvaney, Marc A. Hillmyer, Christopher A. Alabi

Research output: Contribution to journalArticle

Abstract

To date, scalability limitations have hindered the exploration and application of sequence-defined polymers in areas such as synthetic plastics, fibers, rubbers, coatings, and composites. Additionally, the impact of sequence on the properties of cross-linked networks remains largely unknown. To address the need for synthetic methods to generate sequence-defined materials in gram quantities, we developed a strategy involving inexpensive and readily functional vanillin-based monomers to assemble sequence-defined polyurethane oligomers via sequential reductive amination and carbamation. Three oligomers were synthesized with monomer sequence precisely dictated by the placement of reactive side chains during the reductive amination reaction. Avoiding excessive chromatographic purification and solid- or liquid-phase supports enabled synthesis of sequence-defined oligomers on the gram-scale. Remarkably, sequence was shown to influence network topology upon cross-linking, as evidenced by sequence-dependent rubbery moduli values. This work provides one of the first examples of a scalable synthetic route toward sequence-defined thermosets that exhibit sequence-dependent properties.

Original languageEnglish (US)
Pages (from-to)6729-6736
Number of pages8
JournalJournal of the American Chemical Society
Volume142
Issue number14
DOIs
StatePublished - Apr 8 2020

Fingerprint Dive into the research topics of 'Thiol-Ene Networks from Sequence-Defined Polyurethane Macromers'. Together they form a unique fingerprint.

  • Cite this