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Copolymerization of an aryl halide and elemental sulfur as a route to high sulfur content materials

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Abstract

High sulfur-content materials (HSMs) have been investigated for a plethora of applications owing to a combination of desirable properties and the low cost of waste sulfur as a starting monomer. Whereas extended sulfur catenates are unstable with respect to orthorhombic sulfur (S8 rings) at STP, oligomeric/polymeric sulfur chains can be stabilized when they are confined in a supporting matrix. The vast majority of reported HSMs have been made by inverse vulcanization of sulfur and olefins. In the current case, a radical aryl halide–sulfur polymerization (RASP) route was employed to form an HSM (XS81) by copolymerizing elemental sulfur with the xylenol derivative 2,4-dimethyl-3,5-dichlorophenol (DDP). XS81 is a composite of which 81 wt% is sulfur, wherein the sulfur is distributed between cross-linking chains averaging four sulfur atoms in length and trapped sulfur that is not covalently attached to the network. XS81 (flexural strength = 2.0 MPa) exhibits mechanical properties on par with other HSMs prepared by inverse vulcanization. Notably, XS81 retains mechanical integrity over many heat-recast cycles, making it a candidate for facile recyclability. This is the first report of an HSM comprising stabilized polymeric sulfur that has been successfully prepared from a small molecular comonomer by RASP. Preparation of XS81 thus demonstrates a new route to access HSMs using small molecular aryl halides, a notable expansion beyond the olefins required for the well-studied inverse vulcanization route to HSMs from small molecular comonomers.

Graphical abstract: Copolymerization of an aryl halide and elemental sulfur as a route to high sulfur content materials

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Article information


Submitted
11 Nov 2019
Accepted
15 Jan 2020
First published
22 Jan 2020

Polym. Chem., 2020, Advance Article
Article type
Paper

Copolymerization of an aryl halide and elemental sulfur as a route to high sulfur content materials

M. S. Karunarathna, M. K. Lauer, A. G. Tennyson and R. C. Smith, Polym. Chem., 2020, Advance Article , DOI: 10.1039/C9PY01706B

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