Development of a Borane–(Meth)acrylate Photo‐Click Reaction. Issue 31 (24th June 2021)

• Record Type: Journal Article
• Authors: Aubry, Bérengère; Canterel, Rémi; Lansalot, Muriel; Bourgeat‐Lami, Elodie; Airoudj, Aissam; Graff, Bernadette; Dietlin, Céline; Morlet‐Savary, Fabrice; Blahut, Jan; Benda, Ladislav; Pintacuda, Guido; Lacôte, Emmanuel; Lalevée, Jacques
• Is Part Of: Angewandte Chemie international edition. Volume 60:Issue 31(2021)
• Page Start: 17037
• Page End: 17044
• Publication Date: 2021-06-24
• Subjects: boranes -- click chemistry -- photochemistry -- polymerization -- radical reactions; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202103008
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: In the development of 3D printing fuels, there is a need for new photoinitiating systems working under mild conditions and/or leading to polymers with new and/or enhanced properties. In this context, we introduce herein N‐heterocyclic carbene–borane complexes as reagents for a new type of photo‐click reaction, the borane–(meth)acrylate click reaction. Remarkably, the higher bond number of boranes relative to thiols induced an increase of the network density associated with faster polymerization kinetics. Solid‐state NMR evidenced the strong participation of the boron centers on the network properties, while DMA and AFM showed that the materials exhibit improved mechanical properties, as well as reduced solvent swelling. Abstract : N‐Heterocyclic carbene–borane complexes can lead to a photochemically triggered borane–acrylate click reaction, a new type of photo‐click reaction. Because boranes have three substituents they can participate in cross‐linking, unlike thiols in thiol–(meth)acrylate reactions. This generates materials with improved mechanical properties.