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Issue 96, 2014
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Synthesis of poly(sulfonate ester)s by ADMET polymerization

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Many hydrocarbon polymers containing heteroatom defects in the main chain have been investigated as degradable polyethylene-like materials, including aliphatic polyesters. Here, acyclic diene metathesis (ADMET) polymerization was used for the synthesis of aliphatic poly(sulfonate ester)s. The requisite sulfonate ester containing α,ω-diene monomers with varying numbers of methylene groups was synthesized, and their polymerization in the presence of ruthenium-N-heterocyclic (Ru-NHC) alkylidene catalysts was studied. A clear negative neighboring group effect (NNGE) was observed for shorter dienes, either inhibiting polymerization or resulting in low-molecular-weight oligomers. The effect was absent when undec-10-en-1-yl undec-10-ene-1-sulfonate was employed as the monomer, and its ADMET polymerization afforded polymers with appreciable number-average molecular weights of up to 37 000 g mol−1 and a dispersity Đ of 1.8. These polymers were hydrogenated to afford the desired polyethylene-like systems. The thermal and morphological properties of both saturated and unsaturated polymers were investigated. The incorporation of sulfonate ester groups in the polymer backbone offers an interesting alternative to other heteroatoms and helps further the understanding of the effects of these defects on the overall polymer properties.

Graphical abstract: Synthesis of poly(sulfonate ester)s by ADMET polymerization

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Publication details

The article was received on 17 Sep 2014, accepted on 07 Oct 2014 and first published on 07 Oct 2014

Article type: Paper
DOI: 10.1039/C4RA08788G
Citation: RSC Adv., 2014,4, 53967-53974
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    Synthesis of poly(sulfonate ester)s by ADMET polymerization

    R. R. Parkhurst, S. Balog, C. Weder and Y. C. Simon, RSC Adv., 2014, 4, 53967
    DOI: 10.1039/C4RA08788G

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