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Maleimide end-functionalized poly(2-oxazoline)s by the functional initiator route: synthesis and (bio)conjugation

Gil Alvaradejo, Gabriela; Glassner, Mathias; Hoogenboom, Richard; Delaittre, Guillaume

The synthesis of poly(2-ethyl-2-oxazoline)s with a maleimide group at the α chain end was carried out from new sulfonate ester initiators bearing a furan-protected maleimide group. The conditions of the polymerization were optimized for 50 °C using conventional heating (in contrast to microwave irradiation) to counteract the thermal lability of the cycloadduct introduced to protect the maleimide double bond. At this temperature, a tosylate variant was found to be unable to initiate the polymerization after several days. The controlled polymerization of 2-ethyl-2-oxazoline with a nosylate derivative was, however, successful as shown by kinetic experiments monitored by gas chromatography (GC) and size-exclusion chromatography (SEC). Poly(2-ethyl-oxazoline)s of various molar masses (4500 < Mn < 12 000 g mol−1) with narrow dispersity (Đ < 1.2) were obtained. The stability of the protected maleimide functionality during the polymerization, its deprotection, and the reactivity of the deprotected end group by coupling with a model thiol molecule were proven by 1H NMR spectroscopy and electrospray ionization mass spectrometry (ESI-MS). ... mehr

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Verlagsausgabe §
DOI: 10.5445/IR/1000082983
Veröffentlicht am 22.05.2018
DOI: 10.1039/C8RA00948A
Zitationen: 5
Web of Science
Zitationen: 3
Zugehörige Institution(en) am KIT Institut für Technische Chemie und Polymerchemie (ITCP)
Institut für Toxikologie und Genetik (ITG)
Publikationstyp Zeitschriftenaufsatz
Jahr 2018
Sprache Englisch
Identifikator ISSN: 2046-2069
KITopen-ID: 1000082983
HGF-Programm 47.01.01 (POF III, LK 01)
Erschienen in RSC Advances
Band 8
Heft 17
Seiten 9471–9479
Bemerkung zur Veröffentlichung Gefördert durch den KIT-Publikationsfonds
Nachgewiesen in Web of Science
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