Soft Photopolymerizations Initiated by Dye-Sensitized Formation of NHC-Boryl Radicals under Visible Light

Soft Photopolymerizations Initiated by Dye-Sensitized Formation of NHC-Boryl Radicals under Visible Light

A procedure for the production of N-heterocyclic carbene–boryl radicals (NHC-BH2 •) upon visible light irradiation under soft conditions is presented. New acridine orange (dye)/diphenyl disulfide/NHC–BH3 and dye/sulfonium salt/NHC–BH3 three-component initiating systems are introduced for the efficie...

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Veröffentlicht in:Macromolecules 2013-01, Vol.46 (1), p.43-48
Hauptverfasser: Telitel, Sofia, Schweizer, Stéphane, Morlet-Savary, Fabrice, Graff, Bernadette, Tschamber, Théophile, Blanchard, Nicolas, Fouassier, Jean Pierre, Lelli, Moreno, Lacôte, Emmanuel, Lalevée, Jacques
Format: Artikel
Sprache:eng
Schlagworte:
Applied sciences
Chemical Sciences
Exact sciences and technology
Physicochemistry of polymers
Polymerization
Polymers
Polymers and radiations
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Zusammenfassung:A procedure for the production of N-heterocyclic carbene–boryl radicals (NHC-BH2 •) upon visible light irradiation under soft conditions is presented. New acridine orange (dye)/diphenyl disulfide/NHC–BH3 and dye/sulfonium salt/NHC–BH3 three-component initiating systems are introduced for the efficient visible light photopolymerization of trimethylolpropane triacrylate. The new systems could be extendend to polymerization reactions in water (hydroxyethyl acrylate and hydroxyethyl methyl acrylate), which proceeded with strongly improved polydispersity. The chemical mechanisms are investigated through EPR and photolysis experiments.
ISSN:0024-9297
1520-5835
DOI:10.1021/ma302009p