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Rigid Multidimensional Alkoxyamines: A Versatile Building Block Library

Matt, Yannick; Wessely, Isabelle; Gramespacher, Lisa; Tsotsalas, Manuel; Bräse, Stefan

Abstract:
Since the discovery of the “living” free‐radical polymerization, alkoxyamines were widely used in nitroxide‐mediated polymerization (NMP). Most of the known alkoxyamines bear just one functionality with only a few exceptions bearing two or more alkoxyamine units. Herein, we present a library of novel multidimensional alkoxyamines based on commercially available, rigid, aromatic core structures. A versatile approach allows the introduction of different sidechains which have an impact on the steric hindrance and dissociation behavior of the alkoxyamines. The reaction to the alkoxyamines was optimized by implementing a mild and reliable procedure to give all target compounds in high yields. Utilization of biphenyl, p‐terphenyl, 1,3,5‐triphenylbenzene, tetraphenylethylene, and tetraphenyl‐methane results in linear, trigonal, square planar, and tetrahedral shaped alkoxyamines. These building blocks are useful initiators for multifold NMP leading to star‐shaped polymers or as a linker for the nitroxide exchange reaction (NER), to obtain dynamic frameworks with a tunable crosslinking degree and self‐healing abilities.

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Verlagsausgabe §
DOI: 10.5445/IR/1000129406
Veröffentlicht am 05.02.2021
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Institut für Funktionelle Grenzflächen (IFG)
Institut für Biologische und Chemische Systeme (IBCS)
Publikationstyp Zeitschriftenaufsatz
Publikationsmonat/-jahr 01.2021
Sprache Englisch
Identifikator ISSN: 1434-193X, 1099-0690
KITopen-ID: 1000129406
HGF-Programm 47.01.01 (POF III, LK 01) Biol.Netzwerke u.Synth.Regulat. ITG+ITC
Erschienen in European journal of organic chemistry
Verlag Wiley
Band 2021
Heft 2
Seiten 239–245
Vorab online veröffentlicht am 16.12.2020
Schlagwörter Alkoxyamines; Nitroxides; Polymerization; Radical reactions; Synthetic methods
Nachgewiesen in Scopus
Web of Science
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