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Development of a Borane–(Meth)acrylate Photo‐Click Reaction

Bérengère Aubry, Rémi Canterel, Muriel Lansalot, Élodie Bourgeat‐Lami, Aissam Airoudj, Bernadette Graff, Céline Dietlin, Fabrice Morlet‐Savary, Jan Blahut, Ladislav Benda, Guido Pintacuda, Emmanuel Lacôte, Jacques Lalevée

2021Angewandte Chemie International Edition18 citationsDOIOpen Access PDF

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.

Topics & Concepts

BoraneAcrylateContext (archaeology)PolymerizationClick chemistryChemistryPolymer chemistryBoranesSubstituentHydroborationCarbenePhotochemistryMaterials sciencePolymerBoronOrganic chemistryCatalysisMonomerBiologyPaleontologyClick Chemistry and ApplicationsOrganoboron and organosilicon chemistryRadical Photochemical Reactions
Development of a Borane–(Meth)acrylate Photo‐Click Reaction | Litcius