Organocatalyzed Ring‐Opening Polymerization of ( S )‐3‐Benzylmorpholine‐2,5‐Dione

GND
1150443456
Affiliation
Laboratory of Organic and Macromolecular Chemistry (IOMC) Friedrich Schiller University Jena Humboldtstr. 10 07743 Jena Germany
Göppert, Natalie E.;
GND
1258308029
Affiliation
Laboratory of Organic and Macromolecular Chemistry (IOMC) Friedrich Schiller University Jena Humboldtstr. 10 07743 Jena Germany
Dirauf, Michael;
GND
1276149425
Affiliation
Institute for Inorganic and Analytical Chemistry (IAAC) Friedrich Schiller University Jena Humboldtstr. 8 07743 Jena Germany
Liebing, Phil;
GND
1027788505
Affiliation
Laboratory of Organic and Macromolecular Chemistry (IOMC) Friedrich Schiller University Jena Humboldtstr. 10 07743 Jena Germany
Weber, Christine;
GND
113792077
ORCID
0000-0003-4978-4670
Affiliation
Laboratory of Organic and Macromolecular Chemistry (IOMC) Friedrich Schiller University Jena Humboldtstr. 10 07743 Jena Germany
Schubert, Ulrich S.

Abstract 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.

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