2-Azaallyl Anion Initiated Ring-Opening Polymerization of N-Sulfonyl Aziridines: One-Pot Synthesis of Primary Amine-Ended Telechelic Polyaziridines

Ying Wang, Ruhan Yang, Wenyi Luo, Zhunxuan Li, Zhen Zhang, Chuande Wu, Nikos Hadjichristidis

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Using the easily accessible 2-azaallyl anions as initiators, the one-pot synthesis of well-defined primary amine-ended telechelic polyaziridines (α-NH2 PAzs) has been achieved through the ring-opening polymerization (ROP) of N-sulfonyl aziridines followed by hydrolysis of the diphenylketimine moiety (- N=C - Ph2). The 2-azaallyl anions were synthesized from the reaction of diphenylketimine or N-[aryl-methylene]-α-phenylbenzenemethanamine with potassium bis(trimethylsilyl) amide (KHMDS) in situ and used to initiate the ROP of aziridines leading to well-defined α-(Ph2C=N)-α′-aryl-ω-NH PAzs. Along with the diphenylketimine group (- N=C - Ph2), aryl functionalities, such as pyridine and triphenylphosphine moieties, can also be incorporated to the chain end. Chain extension has been applied for the synthesis of poly(N-sulfonyl aziridine)-block-poly(ϵ-caprolactone) (PAz-b-PCL) block copolymers by utilization of the primary amine end group as initiating sites for the ROP of ϵ-caprolactone catalyzed by tin 2-ethyl hexanoate (SnOct2). Taking advantage of this synthetic approach, core cross-linked multiarm star (CCS) polymers with an outermost shell having amino and triphenylphosphine functionalities have been synthesized via "arm-first" strategy.
Original languageEnglish (US)
Pages (from-to)3888-3896
Number of pages9
JournalMacromolecules
Volume52
Issue number10
DOIs
StatePublished - 2019

ASJC Scopus subject areas

  • Materials Chemistry
  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry

Fingerprint

Dive into the research topics of '2-Azaallyl Anion Initiated Ring-Opening Polymerization of N-Sulfonyl Aziridines: One-Pot Synthesis of Primary Amine-Ended Telechelic Polyaziridines'. Together they form a unique fingerprint.

Cite this