Organocatalyzed Ring-Opening Polymerization of (S)-3-Benzylmorpholine-2,5-Dione.
degradable polymers
l-phenylalanine
morpholine-2,5-dione
poly(ester amide)
ring-opening polymerization
Journal
Macromolecular rapid communications
ISSN: 1521-3927
Titre abrégé: Macromol Rapid Commun
Pays: Germany
ID NLM: 9888239
Informations de publication
Date de publication:
Feb 2023
Feb 2023
Historique:
revised:
07
11
2022
received:
29
07
2022
pubmed:
23
11
2022
medline:
10
2
2023
entrez:
22
11
2022
Statut:
ppublish
Résumé
A 3-benzylmorpholine-2,5-dione monomer is synthesized from the natural amino acid l-phenylalanine and characterized by means of nuclear magnetic resonance and infrared spectroscopy, electrospray ionization mass spectrometry, and elemental analysis. Subsequent to preliminary polymerization studies, a well-defined poly(ester amide) homopolymer is synthesized via ring-opening polymerization using a binary catalyst system comprising 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and a 1-(3,5-bis(trifluoromethyl)phenyl)-3-cyclohexylthiourea (TU) cocatalyst with a feed ratio of M/I/DBU/TU = 100/1/1/10. Kinetic studies reveal high controllability of the dispersities and molar masses up to conversions of almost 80%. Analysis by mass spectrometry hints toward excellent end-group fidelity at these conditions. In consequence, utilization of hydroxyl-functionalized poly(ethylene glycol) and poly(2-ethyl-2-oxazoline) as macroinitiators results in amphiphilic block copolymers. Bulk miscibility of the building blocks is indicated by differential scanning calorimetry investigations. As more and more promising new drugs are based on hydrophobic molecules featuring aromatic moieties, the novel polyesteramides seem highly promising materials to be used as potential drug delivery vehicles.
Identifiants
pubmed: 36413677
doi: 10.1002/marc.202200651
doi:
Substances chimiques
Polymers
0
Polyethylene Glycols
3WJQ0SDW1A
Amino Acids
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e2200651Subventions
Organisme : Deutsche Forschungsgemeinschaft
ID : 316213987
Organisme : Federal Ministry of Education and Research of Germany (BMBF)
ID : 13XP5049C
Organisme : Thüringer Aufbaubank
ID : 2016 IZN 0009
Informations de copyright
© 2022 The Authors. Macromolecular Rapid Communications published by Wiley-VCH GmbH.
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