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Reactive imidazole intermediates: simplified synthetic approach to functional aliphatic cyclic carbonates
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.ORCID iD: 0000-0001-7543-5322
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.ORCID iD: 0000-0001-6112-0450
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2014 (English)In: Polymer Chemistry, ISSN 1759-9954, E-ISSN 1759-9962, Vol. 5, no 23, 6651-6655 p.Article in journal (Refereed) Published
Abstract [en]

Reactive imidazole intermediates based on AB(2) and A(3) monomers, i.e. bis(methylol) propionic acid (bis-MPA) and trimethylolpropane (TMP) have successfully been synthesized and isolated on a 100 gram scale via a facile synthetic protocol using 1,1' -carbonyldiimidazole (CDI) as a key reagent. The robustness of the imidazole intermediates as bench stable precursors enabled the synthesis of a library of functional cyclic carbonates bearing relevant functionalities including hydrophilic PEGs, bioactive cholesterol and clickable groups. A number of functional polycarbonates were obtained by ring-opening polymerization, and their relevance in biomedical applications was highlighted by their low cytotoxicity on human dermal fibroblasts (hDF).

Place, publisher, year, edition, pages
Royal Society of Chemistry, 2014. Vol. 5, no 23, 6651-6655 p.
Keyword [en]
Cyclic carbonates, Synthetic approach
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-157251DOI: 10.1039/c4py00911hISI: 000344374500003Scopus ID: 2-s2.0-84908471876OAI: oai:DiVA.org:kth-157251DiVA: diva2:769538
Funder
Knut and Alice Wallenberg Foundation, 2012-0196Swedish Research Council, 2010-453
Note

QC 20141208

Available from: 2014-12-08 Created: 2014-12-08 Last updated: 2017-12-15Bibliographically approved

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Hult, DanielGarcia-Gallego, SandraMalkoch, Michael

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