Issue 28, 2024

Radical polymerisation and thiol–ene post-polymerisation functionalisation of terpenoid acrylates in conventional and renewably sourced organic solvents

Abstract

Geranyl acrylate has been synthesized and polymerized by various radical polymerisation techniques. Due to the structural diversity, a number of post polymerisation functionalization options were explored. Monomer conversion, polymer structure and the molecular weight were assessed by NMR, FT-IR and size exclusion chromatography (SEC). Free radical polymerization and Cu-mediated reversible deactivation radical polymerization (RDRP) were used to synthesise poly(geranyl acrylate) of various molecular weight in both conventional petro-derived organic and bio-based renewably sourced solvents. Cu0 wire-mediated RDRP was found to be a suitable polymerisation method when compared to CuII-mediated photoinduced RDRP giving the optimal living radical polymerisation method for the synthesis of poly(geranyl acrylate) in Cyrene (Mn, SEC = 3000, ĐSEC = 1.25). The residual allylic double bonds provided a useful option for post-polymerization modification. Poly(geranyl acrylate) was subjected to photoinduced thiol–ene reactions, using different thiols with a variety of functional groups. The success of the functionalization reaction was evaluated by NMR, FT-IR spectroscopy, and SEC. In addition, differential scanning calorimetry was used to investigate changes in the thermal properties of the polymer, before and after thiol–ene functionalization.

Graphical abstract: Radical polymerisation and thiol–ene post-polymerisation functionalisation of terpenoid acrylates in conventional and renewably sourced organic solvents

Supplementary files

Article information

Article type
Paper
Submitted
28 mar 2024
Accepted
20 iyn 2024
First published
25 iyn 2024
This article is Open Access
Creative Commons BY license

Polym. Chem., 2024,15, 2862-2872

Radical polymerisation and thiol–ene post-polymerisation functionalisation of terpenoid acrylates in conventional and renewably sourced organic solvents

H. Liu, V. A. Maugein and D. M. Haddleton, Polym. Chem., 2024, 15, 2862 DOI: 10.1039/D4PY00340C

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