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The Anionic Polymerization of a tert-Butyl-Carboxylate-Activated Aziridine

Polymers, 2022-08, Vol.14 (16) [Peer Reviewed Journal]

ISSN: 2073-4360 ;EISSN: 2073-4360

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  • Title:
    The Anionic Polymerization of a tert-Butyl-Carboxylate-Activated Aziridine
  • Author: Giri, Chandan ; Chang, Jen-Yu ; Mbarushimana, Pierre Canisius ; Rupar, Paul A.
  • Subjects: Polymer Science
  • Is Part Of: Polymers, 2022-08, Vol.14 (16)
  • Description: N-Sulfonyl-activated aziridines are known to undergo anionic-ring-opening polymerizations (AROP) to form polysulfonyllaziridines. However, the post-polymerization deprotection of the sulfonyl groups from polysulfonyllaziridines remains challenging. In this report, the polymerization of tert-butyl aziridine-1-carboxylate (BocAz) is reported. BocAz has an electron-withdrawing tert-butyloxycarbonyl (BOC) group on the aziridine nitrogen. The BOC group activates the aziridine for AROP and allows the synthesis of low-molecular-weight poly(BocAz) chains. A 13C NMR spectroscopic analysis of poly(BocAz) suggested that the polymer is linear. The attainable molecular weight of poly(BocAz) is limited by the poor solubility of poly(BocAz) in AROP-compatible solvents. The deprotection of poly(BocAz) using trifluoroacetic acid (TFA) cleanly produces linear polyethyleneimine. Overall, these results suggest that carbonyl groups, such as BOC, can play a larger role in the in the activation of aziridines in anionic polymerization and in the synthesis of polyimines.
  • Publisher: United States: MDPI
  • Language: English
  • Identifier: ISSN: 2073-4360
    EISSN: 2073-4360
  • Source: Open Access: DOAJ Directory of Open Access Journals
    Open Access: PubMed Central
    Geneva Foundation Free Medical Journals at publisher websites
    AUTh Library subscriptions: ProQuest Central
    ROAD: Directory of Open Access Scholarly Resources
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