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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.zeige mehrzeige weniger

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Metadaten
Verfasserangaben:Oliver Kreye, Oguz Türünc, Ansgar Sehlinger, Jenny RackwitzGND, Michael A. R. Meier
DOI:https://doi.org/10.1002/chem.201103341
ISSN:0947-6539
Titel des übergeordneten Werks (Englisch):Chemistry - a European journal
Verlag:Wiley-VCH
Verlagsort:Weinheim
Publikationstyp:Wissenschaftlicher Artikel
Sprache:Englisch
Jahr der Erstveröffentlichung:2012
Erscheinungsjahr:2012
Datum der Freischaltung:26.03.2017
Freies Schlagwort / Tag:Ugi reaction; metathesis; polyamides; polymerization; renewable resources; thiol-ene reactions
Band:18
Ausgabe:18
Seitenanzahl:10
Erste Seite:5767
Letzte Seite:5776
Organisationseinheiten:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert
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