4.7 Article

Polymerizations of 2-(Trimethylsilyl)ethanesulfonyl-activated aziridines

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EUROPEAN POLYMER JOURNAL
卷 169, 期 -, 页码 -

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PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.eurpolymj.2022.111135

关键词

Aziridines; Poly(aziridine)s; Block copolymer; Star-shaped polymer; Anionic polymerization; Desulfonylation

资金

  1. Department of Energy [DE-SC0020282]
  2. University of Alabama
  3. NSF MRI program [CHE1919906]
  4. U.S. Department of Energy (DOE) [DE-SC0020282] Funding Source: U.S. Department of Energy (DOE)

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A novel N-sulfonyl aziridine, N-((2-(trimethylsilyl)ethyl)sulfonyl)-2-methyl-aziridine (SES-MeAz), was synthesized and its controlled anionic ring-opening polymerization was studied. The desulfonylation of poly(SES-MeAz)s to form polypropylene imine (PPI) was achieved under mild conditions using tetrabutylammonium fluoride (TBAF). The first example of the selective removal of a sulfonyl protecting group from a poly(sulfonylazirdine) block copolymer and the first formation of a polysufonylaziridine-block-polypropylene imine copolymer were reported. Successful synthesis of three-armed star-shaped poly(SESMeAz)s with improved solubility compared to linear poly(SESMeAz)s was also demonstrated.
A novel N-sulfonyl aziridine, N-((2-(trimethylsilyl)ethyl)sulfonyl)-2-methyl-aziridine (SES-MeAz) was synthesized, and its controlled anionic ring-opening polymerization to form poly(SES-MeAz) studied. The desulfonylation of poly(SES-MeAz)s can be achieved under mild conditions, with tetrabutylammonium fluoride (TBAF) to form polypropylene imine (PPI), although purification of the PPI was not completely successful. The block copolymer p(pTs-MeAz)-b-p(SES-MeAz), (pTs-MeAz = N-para-tosyl-2-methyl-aziridine) was prepared by a sequential polymerization. The desulfonylation of the block copolymer is the first example of the selective removal of a sulfonyl protecting group from a poly(sulfonylazirdine) block copolymer and this is the first formation of a polysufonylaziridine-block-polypropylene imine copolymer. Three-armed star-shaped poly(SESMeAz)s were also successfully synthesized and exhibited improved solubility compared with linear poly(SESMeAz)s.

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