Direct introduction of hydroxyl groups in polystyrene chain ends prepared by atom-transfer radical polymerization

We report a method to directly introduce a hydroxyl group at the omega chain end of polystyrene prepared by atom-transfer radical polymerization. To achieve the quantitative conversion of the bromine group to a hydroxyl group, the transfer reaction of a carbocation with water was exploited. This transfer reaction is a well-known reaction in cationic polymerization. The quantitative conversion and chemical structures of the hydroxyl-terminated PS were characterized using 1 H nuclear magnetic resonance spectroscopy, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and high-performance liquid chromatography. In addition, alcohol-based compounds were used to introduce acetonide and propane groups into PS-Br. We introduce a facile method to convert the bromine end of the polymer into a hydroxyl group. For this, bromine-terminated polystyrene (PS-Br) was prepared by atom transfer radical polymerization. The bromine groups of the PS-Br could be directly converted to hydroxyl groups by using Ag + as the Lewis acid in water/acetone. The conversion yield was investigated by 1 H nuclear magnetic resonance spectroscopy, high-performance liquid chromatography, and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.