Aziridine termination of living anionic polymerization.
A switch from carbanions to aza-anions is performed by the addition of N-tosylaziridine (TAz) to living poly(styryl) (PS) chains. This is the first example of carbanionic aziridine ring-opening which was previously activated by amidation with a tosyl group to enable nucleophilic ring-opening by the living chain end. Poly(styrene)-tosylaziridines (PS-TAz) with narrow molecular weight distributions and variable molecular weights are synthesized. The removal of the tosyl group and subsequent functionalization is shown, evidencing quantitative transfer to azaanionic species. All polymers are characterized in detail by (1) H NMR spectroscopy, DOSY (1) H NMR spectroscopy, and size exclusion chromatography (SEC). This strategy allows the introduction of amine groups via anionic polymerization in analogy to the well-established epoxide termination.
Max Planck Institute for Polymer Research, Ackermannweg 10, 55128, Mainz, Germany.
Laura
L
Thomi
Frederik R
FR
Wurm
D000838:Anions / Q000737:chemistry; D001388:Aziridines / Q000138:chemical synthesis / Q000737:chemistry*; D002850:Chromatography, Gel; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D058105:Polymerization; D011137:Polystyrenes / Q000737:chemistry
D000838:Anions; D001388:Aziridines; D011137:Polystyrenes; C033132:aziridine
amine-termination; aza-anionic polymerization; poly(aziridine); poly(styrene)