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N-heterocyclic carbenes-borane complexes: A new class of initiators for radical photopolymerization

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 ) 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. 2 •


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Tehfe, MA
Brahmi, MM
Fouassier, JP
Curran, DPcurran@pitt.eduCURRAN
Malacria, M
Fensterbank, L
Lacôte, E
Lalevée, J
Date: 9 March 2010
Date Type: Publication
Journal or Publication Title: Macromolecules
Volume: 43
Number: 5
Page Range: 2261 - 2267
DOI or Unique Handle: 10.1021/ma902492q
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0024-9297
Date Deposited: 20 Mar 2013 16:47
Last Modified: 30 Mar 2021 12:56
URI: http://d-scholarship.pitt.edu/id/eprint/17777

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