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ADMET polymerization of amino-acid-based diene

  • 1,4-Di(homo)allyl-2,5-diketopiperazines are synthesized and polymerized via ADMET using the Hoveyda-Grubbs 2nd generation catalyst. The but-3-enylated diketopiperazine can be converted into unsaturated tertiary polyamide with molar mass of <3000 g mol(-1), whereas the allylated diketopiperazine cannot. Double-bond isomerization occurs regardless of whether or not benzoquinone is present. A polyesteramide with a higher molar mass of ca. 4800 g mol(-1) is obtained by the alternating copolymerization (ALTMET) of 1,4-di(but-3-enyl)-2,5-di ketopiperazine and ethylene glycol diacrylate. A post-polymerization modification of the poly(ester)amides via radical thiol-ene chemistry, however, fails.

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Author:Felix N. Fuehrer, Helmut SchlaadORCiDGND
ISSN:1022-1352 (print)
ISSN:1521-3935 (online)
Parent Title (English):Macromolecular chemistry and physics
Place of publication:Weinheim
Document Type:Article
Year of first Publication:2014
Year of Completion:2014
Release Date:2017/03/27
Tag:acyclic diene metathesis (ADMET) polymerization; amino acids; diketopiperazine; metathesis; step-growth polymerization
First Page:2268
Last Page:2273
Funder:Max Planck Society
Organizational units:Extern / Extern
Peer Review:Referiert