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Fluoride-promoted carbonylation polymerization: A facile step-growth technique to polycarbonates
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.ORCID iD: 0000-0001-7543-5322
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.ORCID iD: 0000-0001-6112-0450
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Coating Technology.ORCID iD: 0000-0002-9200-8004
2017 (English)In: Chemical Science, ISSN 2041-6520, E-ISSN 2041-6539, Vol. 8, no 7, 4853-4857 p.Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
Royal Society of Chemistry , 2017. Vol. 8, no 7, 4853-4857 p.
Keyword [en]
Carbonylation, Fluorine compounds, Glass transition, Monomers, Polycarbonates, Activating reagents, Building blockes, Carbonyldiimidazole, Catalytic polymerization, Efficient catalysts, Growth techniques, Proof of concept, Step-growth polymerizations, Polymerization
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-216581DOI: 10.1039/c6sc05582fISI: 000404617300018Scopus ID: 2-s2.0-85021739063OAI: oai:DiVA.org:kth-216581DiVA: diva2:1154055
Note

QC 20171101

Available from: 2017-11-01 Created: 2017-11-01 Last updated: 2017-11-01Bibliographically approved

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Hult, DanielGarcia-Gallego, SandraMalkoch, Michael

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