N-Heterocyclic carbene-borane radicals as efficient initiating species of photopolymerization reactions under air

Literature Information

Publication Date 2010-11-16
DOI 10.1039/C0PY00296H
Impact Factor 5.582
Authors

Mohamad-Ali Tehfe, Julien Monot, Malika Makhlouf Brahmi, Hélène Bonin-Dubarle, Dennis P. Curran, Max Malacria, Louis Fensterbank, Emmanuel Lacôte, Jacques Lalevée, Jean-Pierre Fouassier


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Abstract

Eight N-heterocyclic carbene-boranes (NHC-boranes) are proposed as new efficient co-initiators for acrylate photopolymerization reactions. They are particularly interesting in aerated conditions, where they help overcome the classical oxygen inhibition. The carbene boryl radicals that are the initiating species have been characterized by their transient absorption spectra obtained in laser flash photolysis (LFP) experiments. Rate constants for the generation of the carbene boryl radicals by hydrogen abstraction with t-butoxyl radical and triplet benzophenone as well as the reactions with oxygen, electron rich and electron poor alkenes, two alkyl halides (CHCl3 and iodopropane) and diphenyliodonium hexafluorophosphate have been measured. The reactivity of N-heterocyclic carbene borane radicals is clearly affected by the NHC substituent.

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