Phthalimidomethyl trithiocarbonate reversible addition−fragmentation chain transfer (RAFT) agents
are effective in imparting living characteristics to radical polymerizations of butyl acrylate (BA) and
N-isopropylacrylamide (NIPAM) and provide a route to end-functional polymers with predictable molecular weight
and narrow molecular weight distributions (e.g., number-average molecular weight for PBA (M̄
n) = 21 300 and
polydispersity (M̄
w/M̄
n) = 1.1 at 96% conversion). End group determination suggests that bimodal molecular
weight distributions and long chain branches in PBA arise by copolymerization of a PBA macromonomer formed
by backbiting β-scission. The S-phthalimidomethyl xanthates provide good control over polymerizations of the
less-activated monomers N-vinylpyrrolidone (NVP) and vinyl acetate (VAc). In the case of PBA with a
trithiocarbonate end or PVAc with a xanthate end, the C−S bond to the thiocarbonylthio end group can be
homolyzed by thermolysis at >180 °C leaving the phthalimidomethyl end group and the ester side groups intact
providing macromonomers, with ω end group −CH2−C(CO2C4H9)(CH2) or −CH2−C(O2CCH3)(CH2)
respectively, as the main products.
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