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Synthesis of poly(cyclohexene oxide)‐ block ‐polystyrene by combination of radical‐promoted cationic polymerization, atom transfer radical polymerization and click chemistry
Author(s) -
Degirmenci Mustafa,
Genli Nasrettin
Publication year - 2010
Publication title -
polymer international
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.592
H-Index - 105
eISSN - 1097-0126
pISSN - 0959-8103
DOI - 10.1002/pi.2800
Subject(s) - cationic polymerization , cyclohexene oxide , chemistry , atom transfer radical polymerization , polymer chemistry , polymerization , alkyne , chain transfer , radical polymerization , cyclohexene , reversible addition−fragmentation chain transfer polymerization , end group , cobalt mediated radical polymerization , ring opening polymerization , organic chemistry , polymer , catalysis
The combination of radical‐promoted cationic polymerization, atom transfer radical polymerization (ATRP) and click chemistry was employed for the efficient preparation of poly(cyclohexene oxide)‐ block ‐polystyrene (PCHO‐ b ‐PSt). Alkyne end‐functionalized poly(cyclohexene oxide) (PCHO‐alkyne) was prepared by radical‐promoted cationic polymerization of cyclohexene oxide monomer in the presence of 1,2‐diphenyl‐2‐(2‐propynyloxy)‐1‐ethanone (B‐alkyne) and an onium salt, namely 1‐ethoxy‐2‐methylpyridinium hexafluorophosphate, as the initiating system. The B‐alkyne compound was synthesized using benzoin photoinitiator and propargyl bromide. Well‐defined bromine‐terminated polystyrene (PSt‐Br) was prepared by ATRP using 2‐oxo‐1,2‐diphenylethyl‐2‐bromopropanoate as initiator. Subsequently, the bromine chain end of PSt‐Br was converted to an azide group to obtain PSt‐N 3 by a simple nucleophilic substitution reaction. Then the coupling reaction between the azide end group in PSt‐N 3 and PCHO‐alkyne was performed with Cu(I) catalysis in order to obtain the PCHO‐ b ‐PSt block copolymer. The structures of all polymers were determined. Copyright © 2010 Society of Chemical Industry