Journal
MACROMOLECULAR CHEMISTRY AND PHYSICS
Volume 215, Issue 22, Pages 2268-2273Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/macp.201400166
Keywords
acyclic diene metathesis (ADMET) polymerization; amino acids; diketopiperazine; metathesis; step-growth polymerization
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Funding
- Max Planck Society
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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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