Iron-catalysed synthesis and chemical recycling of telechelic 1,3-enchained oligocyclobutanes

Megan Mohadjer Beromi, C. Rose Kennedy, Jarod M. Younker, Alex E. Carpenter, Sarah J. Mattler, Joseph A. Throckmorton, Paul J. Chirik

Research output: Contribution to journalArticlepeer-review

Abstract

Closed-loop recycling offers the opportunity to mitigate plastic waste through reversible polymer construction and deconstruction. Although examples of chemical recycling of polymers are known, few have been applied to materials derived from abundant commodity olefinic monomers, which are the building blocks of ubiquitous plastic resins. Here we describe a [2+2] cycloaddition/oligomerization of 1,3-butadiene to yield a previously unrealized telechelic microstructure of (1,n′-divinyl)oligocyclobutane. This material is thermally stable, has stereoregular segments arising from chain-end control, and exhibits high crystallinity even at low molecular weight. Exposure of the oligocyclobutane to vacuum in the presence of the pyridine(diimine) iron precatalyst used to synthesize it resulted in deoligomerization to generate pristine butadiene, demonstrating a rare example of closed-loop chemical recycling of an oligomeric material derived from a commodity hydrocarbon feedstock. [Figure not available: see fulltext.].

Original languageEnglish (US)
Pages (from-to)156-162
Number of pages7
JournalNature chemistry
Volume13
Issue number2
DOIs
StatePublished - Feb 2021

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

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