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Alkyl Triarylstannanecarbodithioates: Synthesis, Crystal Structures, and Efficiency in RAFT Polymerization
Author(s) -
Kulai Ihor,
SaffonMerceron Nathalie,
Voitenko Zoia,
Mazières Stéphane,
Destarac Mathias
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201703412
Subject(s) - chain transfer , raft , alkyl , polymerization , reversible addition−fragmentation chain transfer polymerization , polymer chemistry , chemistry , styrene , nuclear magnetic resonance spectroscopy , acrylate , fragmentation (computing) , radical polymerization , polymer , organic chemistry , copolymer , computer science , operating system
Eight alkyl triarylstannanecarbodithioates were synthesized starting from the corresponding triarylstannyl chlorides. They were fully characterized by IR and 1 H, 13 C, and 119 Sn NMR spectroscopy and mass spectrometry. Their solid‐state structures and geometric parameters were determined and compared to those of other classes of thiocarbonylthio compounds. These new organotin derivatives are efficient reversible chain‐transfer agents for reversible addition–fragmentation chain transfer (RAFT) polymerization of styrene (St) and n ‐butyl acrylate (BA), with controlled number‐average molecular weights and narrow dispersities ( Ð <1.3). In some cases, loss of control of the polymerization was evidenced and supported by the observation of side products by 119 Sn NMR spectroscopy. This phenomenon was attributed to the thermal instability of the Sn‐RAFT terminal group.