Mechanically triggered heterolytic unzipping of a low-ceiling-temperature polymer

Charles E. Diesendruck, Gregory I. Peterson, Heather J. Kulik, Joshua A. Kaitz, Brendan D. Mar, Preston A. May, Scott R. White, Todd J. Martínez, Andrew J. Boydston, Jeffrey S. Moore

Research output: Contribution to journalArticlepeer-review


Biological systems rely on recyclable materials resources such as amino acids, carbohydrates and nucleic acids. When biomaterials are damaged as a result of aging or stress, tissues undergo repair by a depolymerization- repolymerization sequence of remodelling. Integration of this concept into synthetic materials systems may lead to devices with extended lifetimes. Here, we show that a metastable polymer, end-capped poly(o-phthalaldehyde), undergoes mechanically initiated depolymerization to revert the material to monomers. Trapping experiments and steered molecular dynamics simulations are consistent with a heterolytic scission mechanism. The obtained monomer was repolymerized by a chemical initiator, effectively completing a depolymerization- repolymerization cycle. By emulating remodelling of biomaterials, this model system suggests the possibility of smart materials where aging or mechanical damage triggers depolymerization, and orthogonal conditions regenerate the polymer when and where necessary.

Original languageEnglish (US)
Pages (from-to)623-628
Number of pages6
JournalNature Chemistry
Issue number7
StatePublished - Jul 2014

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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