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

Giri, Chandan; Chang, Jen-Yu; Mbarushimana, Pierre Canisius; Rupar, Paul A.

doi:10.3390/polym14163253

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

Journal Article · Wed Aug 10 00:00:00 EDT 2022 · Polymers

DOI:https://doi.org/10.3390/polym14163253· OSTI ID:1880711

; Chang, Jen-Yu; Mbarushimana, Pierre Canisius; Rupar, Paul A.

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.

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Research Organization:: Univ. of Alabama, Tuscaloosa, AL (United States); Univ. of South Alabama, Mobile, AL (United States)

Sponsoring Organization:: USDOE; USDOE Office of Science (SC)

Grant/Contract Number:: SC0020282

OSTI ID:: 1880711

Alternate ID(s):: OSTI ID: 1904299

Journal Information:: Polymers, Journal Name: Polymers Journal Issue: 16 Vol. 14; ISSN POLYCK; ISSN 2073-4360

Publisher:: MDPI AGCopyright Statement

Country of Publication:: Switzerland

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
anionic polymerization
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polymer science
polymer synthesis
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The Anionic Polymerization of a tert-Butyl-Carboxylate-Activated Aziridine

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References (53)

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