Synthesis and characterization of novel quaternary ammonium RAFT agents

Synthesis of three new cationic thio compounds suitable to control free-radical polymerization according to the reversible addition fragmentation chain transfer (RAFT) process (reversible addition fragmentation transfer) is presented. Among them, two bear a quaternary ammonium group in the R group [i.e., N,N-dimethyl-N-(4-(((phenylcarbonothionyl)thio)methyl)benzyl)ethanammonium bromide and N-(4-((((dodecylthio)carbonothioyl)thio)methyl)benzyl)-N,N-dimethylethanammonium bromide, a dithioester and a trithiocarbonate, respectively]. The synthesis of a trithiocarbonate bearing an ammonium group in the Z group [i.e., 2-((11-((benzylthio)carbonothioyl)thio)undecanoyl)oxy)-N,N,N-trimethylammonium iodide] is also presented. Another three thio co mpounds, namely 1,4-phenylenebis(methylene)dibenzenecarbodithioate, dido decyl-1,4-phenylenebis(methylene)bistrithiocarbonate, and 11-(((benzylthio)carbono thioyl)thio)undecanoic acid, identified as other potentially interesting mono-or difunctional RAFT agents, which were obtained as side products or intermediates, were isolated and fully characterized.