Synthesis of novel trithiocarbonate and allyl sulfide containing monomers

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.