Abstract

In most synthetic elastomers, changing the physical properties by monomer choice also results in a change to the crystallinity of the material, which manifests through alteration of its mechanical performance. Using organocatalyzed stereospecific additions of thiols to activated alkynes, high‐molar‐mass elastomers were isolated via step‐growth polymerization. The resulting controllable double‐bond stereochemistry defines the crystallinity and the concomitant mechanical properties as well as enabling the synthesis of materials that retain their excellent mechanical properties through changing monomer composition. Using this approach to elastomer synthesis, further end group modification and toughening through vulcanization strategies are also possible. The organocatalytic control of stereochemistry opens the realm to a new and easily scalable class of elastomers that will have unique chemical handles for functionalization and post synthetic processing.

Highlights

  • In most synthetic elastomers, changing the physical properties by monomer choice results in a change to the crystallinity of the material, which manifests through alteration of its mechanical performance

  • Using organocatalyzed stereospecific additions of thiols to activated alkynes, high-molarmass elastomers were isolated via step-growth polymerization

  • Natural rubber and gutta percha are homopolymers of poly(cisisoprene) and poly(trans-isoprene) respectively. While these materials differ by only the double bonds of the backbone, the superior elastomeric properties of natural rubber[2] are attributed to the enhanced chain packing afforded by its stereochemical orientation.[3]

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Summary

Introduction

Abstract: In most synthetic elastomers, changing the physical properties by monomer choice results in a change to the crystallinity of the material, which manifests through alteration of its mechanical performance. The resulting controllable double-bond stereochemistry defines the crystallinity and the concomitant mechanical properties as well as enabling the synthesis of materials that retain their excellent mechanical properties through changing monomer composition.

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Conclusion

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