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Substituent Effects on RAFT Polymerization with Benzyl Aryl Trithiocarbonates
Author(s) -
Bicciocchi Erika,
Chong Yen K.,
Giorgini Loris,
Moad Graeme,
Rizzardo Ezio,
Thang San H.
Publication year - 2010
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.200900557
Subject(s) - raft , polymerization , chemistry , aryl , substituent , styrene , dispersity , chain transfer , polymer chemistry , reversible addition−fragmentation chain transfer polymerization , trifluoromethyl , medicinal chemistry , copolymer , radical polymerization , organic chemistry , polymer , alkyl
The RAFT polymerization of styrene in the presence of benzyl aryl trithiocarbonate RAFT agents (Z′SC(=S)SR) has been studied. The values of the apparent transfer constants $\left( {C_{{\rm tr}}^{{\rm app}} } \right)$ of the benzyl aryl trithiocarbonates (0.029 M ) in bulk styrene polymerization at 110 °C fall within the range 10–25 depending on substituents on the aryl ring (Z′) and are higher than that of benzyl dodecyl trithiocarbonate 1 for which $C_{{\rm tr}}^{{\rm app}}$ was determined to be 9.4. There is a trend for higher transfer constant, lower dispersity product and better control over polymerization with more electron‐withdrawing substituents with the most active in the series studied being the 3,5‐bis(trifluoromethyl)phenyl derivative.