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Direct introduction of hydroxyl groups in polystyrene chain ends prepared by atom-transfer radical polymerization
Polymer Journal ( IF 2.8 ) Pub Date : 2019-09-04 , DOI: 10.1038/s41428-019-0250-z
Kyoungho Kim , Min Guk Seo , Jinyoung Jung , Junyoung Ahn , Taihyun Chang , Heung Bae Jeon , Hyun-jong Paik

Abstract 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.

中文翻译:

在原子转移自由基聚合制备的聚苯乙烯链端直接引入羟基

摘要 我们报告了一种在原子转移自由基聚合制备的聚苯乙烯的 omega 链末端直接引入羟基的方法。为了实现溴基团向羟基的定量转化,利用了碳正离子与水的转移反应。这种转移反应是阳离子聚合中众所周知的反应。使用 1 H 核磁共振光谱、基质辅助激光解吸/电离飞行时间质谱和高效液相色谱表征了羟基封端的 PS 的定量转化和化学结构。此外,醇基化合物用于将丙酮化物和丙烷基团引入 PS-Br。我们介绍了一种将聚合物的溴端转化为羟基的简便方法。为了这,通过原子转移自由基聚合制备溴封端聚苯乙烯(PS-Br)。通过在水/丙酮中使用 Ag + 作为路易斯酸,可以将 PS-Br 的溴基团直接转化为羟基。通过 1 H 核磁共振光谱、高效液相色谱和基质辅助激光解吸/电离飞行时间质谱法研究转化率。
更新日期:2019-09-04
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