In:
Macromolecular Rapid Communications, Wiley, Vol. 39, No. 23 ( 2018-12)
Abstract:
In a two‐step synthesis, five different alkyl‐substituted morpholine‐2,5‐dione monomers were synthesized from the natural amino acids glycine, alanine, valine, leucine, and isoleucine. The heterocyclic compounds crystallize in a boat‐like conformation and are polymerized via 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD)‐catalyzed ring‐opening polymerization (ROP) in tetrahydrofuran. Well‐defined polymers could be obtained from the monomers based on valine, leucine, and isoleucine at a feed ratio of M/I/TBD = 100/1/0.5. Kinetic studies of the ROP reveal that the molar masses and dispersities (Đ 〈 1.2) could be well controlled, as confirmed by size exclusion chromatography and 1 H NMR spectroscopy. At conversions above 50%, the polymerization rate decreases and the dispersity slightly increases, presumably due to transesterification. Matrix‐assisted laser desorption time‐of‐flight mass spectrometry indicates the presence of polymer chains with α‐end groups derived from the initiator.
Type of Medium:
Online Resource
ISSN:
1022-1336
,
1521-3927
DOI:
10.1002/marc.201800433
Language:
English
Publisher:
Wiley
Publication Date:
2018
detail.hit.zdb_id:
1475027-2