Upcycling of Polybutadiene Facilitated by Selenium-Mediated Allylic Amination |
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Authors: | Mercie N. Hodges Matthew J. Elardo Jinyoung Seo Alexander F. Dohoda Prof. Dr. Forrest E. Michael Prof. Dr. Matthew R. Golder |
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Affiliation: | 1. Department of Chemistry, University of Washington, 36 Bagley Hall, Seattle, WA 98195 USA;2. Department of Chemistry & Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138 USA |
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Abstract: | Accumulation of end-of-life plastics presents ongoing environmental concerns. One strategy to solve this grand challenge is to invent new techniques that modify post-consumer waste and impart new functionality. While promising approaches for the chemical upcycling of commodity polyolefins and polyaromatics exist, analogous approaches to repurpose unsaturated polymers (e.g., polybutadiene) are scarce. In this work, we propose a method to upcycle polybutadiene, one of the most widely used commercial rubbers, via a mild, metal-free allylic amination reaction. The resulting materials have tunable thermal and surface wetting properties as a function of both sulfonamide identity and grafting density. Importantly, this approach maintains the parent alkene microstructure without evidence of olefin reduction, olefin transposition, and/or chain scission. Based on these findings, we anticipate future applications in the remediation of complex elastomers and vulcanized rubbers. |
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Keywords: | C−H Functionalization Polymers Post-Polymerization Modification Selenium Upcycling |
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