Tehfe, MA and Brahmi, MM and Fouassier, JP and Curran, DP and Malacria, M and Fensterbank, L and Lacôte, E and Lalevée, J
(2010)
N-heterocyclic carbenes-borane complexes: A new class of initiators for radical photopolymerization.
Macromolecules, 43 (5).
2261 - 2267.
ISSN 0024-9297
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Abstract
Newly discovered N-heterocyclic carbene-boryl radicals (NHC-BH 2•) derived from readily available N-heterocyclic carbene-boranes are found to be efficient initiators for acrylate photopolymerization. Laser flash photolysis (LFP) experiments were used to generate three carbene-boryl radicals, which were characterized by their transient absorption spectra with the aid of DFT calculations. Rate constants were measured for the generation of the carbene-boryl radicals by hydrogen abstraction with tert--butoxyl radical, a ketophosphonyl radical, and triplet benzophenone. Rate constants were also measured for the reactions of the carbene-boryl radicals with oxygen, three alkenes, two alkyl chlorides, and diphenyliodonium hexafluorophosphate. The observed trends were interpreted with the aid of measured oxidation potentials of the carbene-boranes and calculated ionization potentials of the carbene-boryls. N-Heterocyclic carbeneboranes show excellent potential as both photopolymerization co-initiators and mediators of small molecule radical reactions, and these results will help guide further development in both fields. © 2010 American Chemical Society.
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