Development of a Borane-(Meth)acrylate Photo-Click Reaction

Angew Chem Int Ed Engl. 2021 Jul 26;60(31):17037-17044. doi: 10.1002/anie.202103008. Epub 2021 Jun 24.

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.

Keywords: boranes; click chemistry; photochemistry; polymerization; radical reactions.