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Protected amine-functional initiators for the synthesis of α-amine homo- and heterotelechelic poly(2-ethyl-2-oxazoline)s

Title data

Mazrad, Zihnil A. I. ; Lai, May ; Davis, Thomas P. ; Nicolazzo, Joseph A. ; Thurecht, Kristofer J. ; Leiske, Meike N. ; Kempe, Kristian:
Protected amine-functional initiators for the synthesis of α-amine homo- and heterotelechelic poly(2-ethyl-2-oxazoline)s.
In: Polymer Chemistry. Vol. 13 (2022) Issue 30 . - pp. 4436-4445.
ISSN 1759-9954
DOI: https://doi.org/10.1039/D2PY00649A

Official URL: Volltext

Abstract in another language

Polymers bearing amine moieties are highly valuable for their ability to conjugate and/or complex a variety of molecules. However, their incorporation into synthetic macromolecules remains challenging. Poly(2-oxazolines) (POx) are a highly functional class of polymers, which through the choice of polymerization components or post-polymerization modifications, can be furnished with a large range of functional groups. Here, we explored their potential for the preparation of α-amine telechelic macromolecules through a comprehensive comparison of different amine-containing cationic ring-opening polymerization (CROP) initiators comprised of the amine protecting groups tert-butyloxycarbonyl (BOC) and phthalimide and the counterions tosylate (Tos) and bromide (Br). Polymerization kinetics of 2-ethyl-2-oxazoline (EtOx) and stability tests revealed the commercially available phthalimide-NH2-C3-Br as the most suitable initiator for achieving the highest degree of control over the polymerization. The polymerization initiated by this new initiator at 140 °C under microwave irradiation was characterized by a stable protected amine group, and fast initiation, and delivered well-defined poly(2-ethyl-2-oxazoline)s (PEtOx). α-Amine telechelic PEtOx were subsequently synthesized using different terminating agents, enabling the future preparation of tailored aminated POx-based architectures.

Further data

Item Type: Article in a journal
Refereed: Yes
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Junior Professor Sustainable and Functional Polymer Systems > Junior Professor Sustainable and Functional Polymer Systems - Juniorprof. Dr. Meike Leiske
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Junior Professor Sustainable and Functional Polymer Systems
Result of work at the UBT: No
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 18 Jan 2023 14:38
Last Modified: 13 Mar 2023 08:44
URI: https://eref.uni-bayreuth.de/id/eprint/73434