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Optically Active Polymer Via One‐Pot Combination of Chemoenzymatic Transesterification and RAFT Polymerization: Synthesis and Its Application in Hybrid Silica Particles
Author(s) -
Huang Zengfang,
Fu Changkui,
Wang Shiqi,
Yang Bin,
Wang Xing,
Zhang Qingsong,
Yuan Jinying,
Tao Lei,
Wei Yen
Publication year - 2015
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.201500106
Subject(s) - polymerization , chain transfer , dispersity , reversible addition−fragmentation chain transfer polymerization , polymer chemistry , polymer , transesterification , monomer , raft , materials science , chemistry , radical polymerization , organic chemistry , catalysis
A novel strategy for the preparation of hybrid particles of optically active polymer and silica is developed via combination of chemoenzymatic transesterification, reversible addition‐fragmentation chain transfer (RAFT) polymerization, and click reaction for the first time. During this procedure, Novozym 435 is employed to catalyze the transesterification between 2,2,2‐trifluoethyl methacrylate monomer and 2‐octanol to form the target monomer (R)‐OMA, which synchronously participates in RAFT polymerization to obtain a new polymer with transformed optically active side groups. Compared with RAFT polymerization, the transesterification reaction is much faster, with conversion ratio reaching 93% after 7 h; subsequently, the polymerization is nearly homo‐polymerization of (R)‐OMA. The molar fraction of (R)‐OMA in the final polymer is about 97.8% with controlled molecular weight ( M n ≈ 6840 g mol −1 ) and a narrow polydispersity index (≈1.25). Finally, the hybrid particles of silica and optically active polymer P((R)‐OMA) are obtained by the thiol‐ene click reaction. The Fourier transform infrared, X‐ray photoelectron spectroscopy, and transmission electron microscopy results exhibit the successful graft of P((R)‐OMA) polymer to the silica surface, and the P((R)‐OMA) polymer in the hybrid particles is about 10 wt% from the TGA curves. These as‐prepared hybrid particles combine excellent mechanical stability of silica and good chirality of polymer, making them promising for chromatographic resolution, catalytic synthesis, and (stereo‐) selectivity applications.