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Thioacetate‐Based Initiators for the Synthesis of Thiol‐End‐Functionalized Poly(2‐oxazoline)s

Gil Alvaradejo, Gabriela; Glassner, Mathias; Kumar, Ravi; Trouillet, Vanessa; Welle, Alexander; Wang, Yangxin; Rosa, Victor R.; Sekula‐Neuner, Sylwia; Hirtz, Michael; Hoogenboom, Richard; Delaittre, Guillaume

New functional initiators for the cationic ring‐opening polymerization of 2‐alkyl‐2‐oxazolines are described to introduce a thiol moiety at the α terminus. Both tosylate and nosylate initiators carrying a thioacetate group are obtained in multigram scale, from commercial reagents in two steps, including a phototriggered thiol–ene radical addition. The nosylate derivative gives access to a satisfying control over the cationic ring‐opening polymerization of 2‐ethyl‐2‐oxazoline, with dispersity values lower than 1.1 during the entire course of the polymerization, until full conversion. Cleavage of the thioacetate end group is rapidly achieved using triazabicyclodecene, thereby leading to a mercapto terminus. The latter gives access to a new subgeneration of α‐functional poly(2‐oxazoline)s (butyl ester, N‐hydroxysuccinimidyl ester, furan) by Michael addition with commercial (meth)acrylates. The amenability of the mercapto‐poly(2‐ethyl‐2‐oxazoline) for covalent surface patterning onto acrylated surfaces is demonstrated in a microchannel cantilever spotting (µCS) experiment, characterized by X‐ray photoelectron spectroscopy (XPS) and time‐of‐flight secondary‐ion mass spectrometry (ToF‐SIMS).

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Verlagsausgabe §
DOI: 10.5445/IR/1000123346
Veröffentlicht am 12.10.2020
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Angewandte Materialien - Energiespeichersysteme (IAM-ESS)
Institut für Biologische und Chemische Systeme (IBCS)
Institut für Funktionelle Grenzflächen (IFG)
Institut für Nanotechnologie (INT)
Karlsruhe Nano Micro Facility (KNMF)
Publikationstyp Zeitschriftenaufsatz
Publikationsdatum 07.09.2020
Sprache Englisch
Identifikator ISSN: 1022-1336, 1521-3927
KITopen-ID: 1000123346
HGF-Programm 47.01.01 (POF III, LK 01) Biol.Netzwerke u.Synth.Regulat. ITG+ITC
Weitere HGF-Programme 49.02.07 (POF III, LK 02) XPS
Erschienen in Macromolecular rapid communications
Verlag John Wiley and Sons
Band 41
Heft 18
Seiten Art.Nr. 2000320
Vorab online veröffentlicht am 16.08.2020
Schlagwörter KNMF 2020-024-029418 ToF-SIMS XPS DPN
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