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Structurally diverse polyamides obtained from monomers derived via the Ugi multicomponent reaction

  • The combination of the Ugi four-component reaction (Ugi-4CR) with acyclic diene metathesis (ADMET) or thiolene polymerization led to the formation of poly-1-(alkylcarbamoyl) carboxamides, a new class of substituted polyamides with amide moieties in the polymer backbone, as well as its side chains. 10-Undecenoic acid, obtained by pyrolysis of ricinoleic acid, the main fatty acid of castor oil, was used as the key renewable building block. The use of different primary amines, as well as isonitriles (isocyanides) for the described Ugi reactions provided monomers with high structural diversity. Furthermore, the possibility of versatile post-modification of functional groups in the side chains of the corresponding polymers should be of considerable interest in materials science. The obtained monomers were polymerized by ADMET, as well as thiolene, chemistry and all polymers were fully characterized. Finally, ortho-nitrobenzylamide-containing polyamides obtained by this route were shown to be photoresponsive and exhibited a dramatic changeThe combination of the Ugi four-component reaction (Ugi-4CR) with acyclic diene metathesis (ADMET) or thiolene polymerization led to the formation of poly-1-(alkylcarbamoyl) carboxamides, a new class of substituted polyamides with amide moieties in the polymer backbone, as well as its side chains. 10-Undecenoic acid, obtained by pyrolysis of ricinoleic acid, the main fatty acid of castor oil, was used as the key renewable building block. The use of different primary amines, as well as isonitriles (isocyanides) for the described Ugi reactions provided monomers with high structural diversity. Furthermore, the possibility of versatile post-modification of functional groups in the side chains of the corresponding polymers should be of considerable interest in materials science. The obtained monomers were polymerized by ADMET, as well as thiolene, chemistry and all polymers were fully characterized. Finally, ortho-nitrobenzylamide-containing polyamides obtained by this route were shown to be photoresponsive and exhibited a dramatic change of their properties upon irradiation with light.show moreshow less

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Metadaten
Author details:Oliver Kreye, Oguz Türünc, Ansgar Sehlinger, Jenny RackwitzGND, Michael A. R. Meier
DOI:https://doi.org/10.1002/chem.201103341
ISSN:0947-6539
Title of parent work (English):Chemistry - a European journal
Publisher:Wiley-VCH
Place of publishing:Weinheim
Publication type:Article
Language:English
Year of first publication:2012
Publication year:2012
Release date:2017/03/26
Tag:Ugi reaction; metathesis; polyamides; polymerization; renewable resources; thiol-ene reactions
Volume:18
Issue:18
Number of pages:10
First page:5767
Last Page:5776
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer review:Referiert
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