Unprecedented Bifunctional Chemistry of Bis(acyl)phosphane Oxides in Aqueous and Alcoholic Media

Max Schmallegger, Anna Eibel, Jan P. Menzel, Anne Marie Kelterer, Michal Zalibera, Christopher Barner-Kowollik, Hansjörg Grützmacher, Georg Gescheidt*

*Korrespondierende/r Autor/in für diese Arbeit

Publikation: Beitrag in einer FachzeitschriftArtikel

Abstract

Tailor-made photoinitiators play an important role for efficient radical polymerisations in aqueous media, especially in hydrogel manufacturing. Bis(acyl)phosphane oxides (BAPOs) are among the most active initiators. Herein, we show that they display a remarkable photochemistry in aqueous and alcoholic media: Photolysis of BAPOs in the presence of water or alcohols provides a new delocalized π-radical, which does not participate in the polymerization. It either converts into a monoacylphosphane oxide acting as a secondary photoactive species or it works as a one-electron reducing agent. Upon the electron-transfer process, it again produces a dormant photoinitiator. We have established the structure and the chemistry of this π radical using steady-state and time-resolved (CIDEP) EPR together with ESI-MS, NMR spectroscopy, and DFT calculations. Our results show that bis(acyl)phosphane oxides act as bifunctional reagents when applied in aqueous and alcoholic media.

Originalspracheenglisch
Seiten (von - bis)8982-8986
Seitenumfang5
FachzeitschriftChemistry - a European Journal
Jahrgang25
Ausgabenummer38
DOIs
PublikationsstatusVeröffentlicht - 5 Jul 2019

ASJC Scopus subject areas

  • !!Catalysis
  • Organische Chemie

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