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Issue 7, 2017
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Fluoride-promoted carbonylation polymerization: a facile step-growth technique to polycarbonates

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Abstract

Fluoride-Promoted Carbonylation (FPC) polymerization is herein presented as a novel catalytic polymerization methodology that complements ROP and unlocks a greater synthetic window to advanced polycarbonates. The overall two-step strategy is facile, robust and capitalizes on the synthesis and step-growth polymerization of bis-carbonylimidazolide and diol monomers of 1,3- or higher configurations. Cesium fluoride (CsF) is identified as an efficient catalyst and the bis-carbonylimidazolide monomers are synthesized as bench-stable white solids, easily obtained on 50–100 g scales from their parent diols using cheap commercial 1,1′-carbonyldiimidazole (CDI) as activating reagent. The FPC polymerization works well in both solution and bulk, does not require any stoichiometric additives or complex settings and produces only imidazole as a relatively low-toxicity by-product. As a proof-of-concept using only four diol building-blocks, FPC methodology enabled the synthesis of a unique library of polycarbonates covering (i) rigid, flexible and reactive PC backbones, (ii) molecular weights 5–20 kg mol−1, (iii) dispersities of 1.3–2.9 and (iv) a wide span of glass transition temperatures, from −45 up to 169 °C.

Graphical abstract: Fluoride-promoted carbonylation polymerization: a facile step-growth technique to polycarbonates

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Publication details

The article was received on 21 Dec 2016, accepted on 03 May 2017 and first published on 04 May 2017


Article type: Edge Article
DOI: 10.1039/C6SC05582F
Citation: Chem. Sci., 2017,8, 4853-4857
  • Open access: Creative Commons BY-NC license
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    Fluoride-promoted carbonylation polymerization: a facile step-growth technique to polycarbonates

    J. V. Olsson, D. Hult, S. García-Gallego and M. Malkoch, Chem. Sci., 2017, 8, 4853
    DOI: 10.1039/C6SC05582F

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