Journal
EUROPEAN POLYMER JOURNAL
Volume 95, Issue -, Pages 746-755Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.eurpolymj.2017.07.005
Keywords
N-Heterocyclic carbene; Organocatalysis; Functional initiators; Polyaziridines
Categories
Funding
- French Ministry of Education and Research
- Deutsche Forschungsgemeinschaft [WU 750 7/1]
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Polyaziridines (PAz) were synthesized for the first time by the 1,3-bis(isopropyl)-4,5(dimethyl) imidazol-2-ylidene-organocatalyzed ring-opening polymerization (OROP) of 2-alkyl-N-p-toluenesulfonyl aziridine (alkyl = methyl or phenyl), in the presence of both functional activated amine and non-functional non-activated amine initiators. Thus, not only an allyl-functionalized N-sulfonyl amine could serve as initiator, but also trimethylsilyl azide allowed introducing an allyl and an azido functionality in a-position of PAz chains, respectively. A non-activated and commercially available secondary amine, such as di-n-butylamine, also effectively initiated the OROP of N-tosylaziridines. Excellent control over molar masses, high chain-end fidelity and narrow dispersities (D <= 1.20) were achieved, as attested by NMR spectroscopy, size exclusion chromatography and MALDI ToF mass spectrometry. PAz precursors consisting of the alkene or the azido functionality could further be derivatized, highlighting the accessibility of those functional groups. Overall, this N-heterocyclic carbene-OROP methodology offers a metal-free route to well-defined alpha-functionalized PAz.
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