Olefin metathesis-based chemically recyclable polymers enabled by fused-ring monomers

Devavrat Sathe; Junfeng Zhou; Hanlin Chen; Hsin Wei Su; Wei Xie; Tze Gang Hsu; Briana R. Schrage; Travis Smith; Christopher J. Ziegler; Junpeng Wang

doi:10.1038/s41557-021-00748-5

Olefin metathesis-based chemically recyclable polymers enabled by fused-ring monomers

Devavrat Sathe, Junfeng Zhou, Hanlin Chen, Hsin Wei Su, Wei Xie, Tze Gang Hsu, Briana R. Schrage, Travis Smith, Christopher J. Ziegler, Junpeng Wang

Research output: Contribution to journal › Article › peer-review

142 Scopus citations

Abstract

A promising solution to address the challenges in plastics sustainability is to replace current polymers with chemically recyclable ones that can depolymerize into their constituent monomers to enable the circular use of materials. Despite some progress, few depolymerizable polymers exhibit the desirable thermal stability and strong mechanical properties of traditional polymers. Here we report a series of chemically recyclable polymers that show excellent thermal stability (decomposition temperature >370 °C) and tunable mechanical properties. The polymers are formed through ring-opening metathesis polymerization of cyclooctene with a trans-cyclobutane installed at the 5 and 6 positions. The additional ring converts the non-depolymerizable polycyclooctene into a depolymerizable polymer by reducing the ring strain energy in the monomer (from 8.2 kcal mol^–1 in unsubstituted cyclooctene to 4.9 kcal mol^–1 in the fused ring). The fused-ring monomer enables a broad scope of functionalities to be incorporated, providing access to chemically recyclable elastomers and plastics that show promise as next-generation sustainable materials. [Figure not available: see fulltext.]

Original language	English
Pages (from-to)	743-750
Number of pages	8
Journal	Nature Chemistry
Volume	13
Issue number	8
DOIs	https://doi.org/10.1038/s41557-021-00748-5
State	Published - Aug 2021
Externally published	Yes

Funding

This work is supported by the University of Akron. The computational resources were provided by Extreme Science and Engineering Discovery Environment (TG-CHE190099). The single-crystal structures were characterized with an X-ray diffractometer supported by the National Science Foundation (CHE-0840446 to C.J.Z.). We thank S. Wang for helpful discussion and K. Williams-Pavlantos and C. Wesdemiotis for conducting the MS analysis.

Funders	Funder number
National Science Foundation	CHE-0840446
University of Akron

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title = "Olefin metathesis-based chemically recyclable polymers enabled by fused-ring monomers",

abstract = "A promising solution to address the challenges in plastics sustainability is to replace current polymers with chemically recyclable ones that can depolymerize into their constituent monomers to enable the circular use of materials. Despite some progress, few depolymerizable polymers exhibit the desirable thermal stability and strong mechanical properties of traditional polymers. Here we report a series of chemically recyclable polymers that show excellent thermal stability (decomposition temperature >370 °C) and tunable mechanical properties. The polymers are formed through ring-opening metathesis polymerization of cyclooctene with a trans-cyclobutane installed at the 5 and 6 positions. The additional ring converts the non-depolymerizable polycyclooctene into a depolymerizable polymer by reducing the ring strain energy in the monomer (from 8.2 kcal mol–1 in unsubstituted cyclooctene to 4.9 kcal mol–1 in the fused ring). The fused-ring monomer enables a broad scope of functionalities to be incorporated, providing access to chemically recyclable elastomers and plastics that show promise as next-generation sustainable materials. [Figure not available: see fulltext.]",

author = "Devavrat Sathe and Junfeng Zhou and Hanlin Chen and Su, {Hsin Wei} and Wei Xie and Hsu, {Tze Gang} and Schrage, {Briana R.} and Travis Smith and Ziegler, {Christopher J.} and Junpeng Wang",

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AU - Sathe, Devavrat

AU - Zhou, Junfeng

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AU - Su, Hsin Wei

AU - Xie, Wei

AU - Hsu, Tze Gang

AU - Schrage, Briana R.

AU - Smith, Travis

AU - Ziegler, Christopher J.

AU - Wang, Junpeng

PY - 2021/8

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N2 - A promising solution to address the challenges in plastics sustainability is to replace current polymers with chemically recyclable ones that can depolymerize into their constituent monomers to enable the circular use of materials. Despite some progress, few depolymerizable polymers exhibit the desirable thermal stability and strong mechanical properties of traditional polymers. Here we report a series of chemically recyclable polymers that show excellent thermal stability (decomposition temperature >370 °C) and tunable mechanical properties. The polymers are formed through ring-opening metathesis polymerization of cyclooctene with a trans-cyclobutane installed at the 5 and 6 positions. The additional ring converts the non-depolymerizable polycyclooctene into a depolymerizable polymer by reducing the ring strain energy in the monomer (from 8.2 kcal mol–1 in unsubstituted cyclooctene to 4.9 kcal mol–1 in the fused ring). The fused-ring monomer enables a broad scope of functionalities to be incorporated, providing access to chemically recyclable elastomers and plastics that show promise as next-generation sustainable materials. [Figure not available: see fulltext.]

AB - A promising solution to address the challenges in plastics sustainability is to replace current polymers with chemically recyclable ones that can depolymerize into their constituent monomers to enable the circular use of materials. Despite some progress, few depolymerizable polymers exhibit the desirable thermal stability and strong mechanical properties of traditional polymers. Here we report a series of chemically recyclable polymers that show excellent thermal stability (decomposition temperature >370 °C) and tunable mechanical properties. The polymers are formed through ring-opening metathesis polymerization of cyclooctene with a trans-cyclobutane installed at the 5 and 6 positions. The additional ring converts the non-depolymerizable polycyclooctene into a depolymerizable polymer by reducing the ring strain energy in the monomer (from 8.2 kcal mol–1 in unsubstituted cyclooctene to 4.9 kcal mol–1 in the fused ring). The fused-ring monomer enables a broad scope of functionalities to be incorporated, providing access to chemically recyclable elastomers and plastics that show promise as next-generation sustainable materials. [Figure not available: see fulltext.]

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Olefin metathesis-based chemically recyclable polymers enabled by fused-ring monomers

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