Synthesis of novel trithiocarbonate and allyl sulfide containing monomers

Abstract

In this study, we present a mild, efficient, and high yield synthesis of a variety of trithiocarbonates and allyl sulphide-containing AFT (addition–fragmentation termination) monomers containing terminal (meth)acrylate functional groups. The trithiocarbonate moiety core was synthesized with reaction yields often above 95%. Synthesis of monomers with allyl sulphide cores gave yields ranging from 48–92%. These monomers, designated as CRAFT (Controllable Reversible Addition Chain Transfer) monomers, offer the ability to control the mechanical and polymerization properties of the resulting thiol-Michael and chain-growth polymer networks in a previously unattainable manner. The triothiocarbonates reached 70–81% acrylate conversion in 10–200 s of light exposure while the allyl sulphide monomers reached 74–85% conversion in 10–50 s.