A general method for functionalisation of microgel particles with primary amines using click chemistry

A general method for functionalisation of microgel particles with primary amines using click chemistry
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DOI:
10.1016/j.polymer.2013.12.022
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发表时间:
2014-01-30
期刊:
影响因子:
4.6
通讯作者:
Saunders, Brian R.
Saunders, Brian R.
中科院分区:
化学2区
文献类型:
--
作者:
Farley, Robert;Saunders, Brian R.

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在这项研究中,我们介绍了一种使用一步铜催化叠氮化物-炔环加成 (CuAAC) 反应用伯胺基团功能化微凝胶颗粒的通用方法。制备了三个不同系列的含有共聚丙烯酸丙炔酯 (PA) 的微凝胶,然后使用 CuAAC 与 2-叠氮基-1-乙胺 (AEA) 反应。微凝胶含有聚(丙烯酸乙酯)(PEA)、聚(2-乙烯基吡啶)(PVP)或聚(N-异丙基丙烯酰胺)(PNP)。通过元素分析和 FTIR 评估 AEA 对含有 PA(即 PX-PA)的微凝胶进行官能化,得到伯胺官能化颗粒(PX-PA-AEA)。对于每种 PX-PA-AEA 微凝胶,AEA 与 PA 的反应是定量的(X = EA、VP 和 NP)。 PX-PA-AEA 系统通常表现出比未点击的 PX-PA 颗粒更大的 pH 引发的膨胀和 zeta 电位。结果还表明,PA 通过充当交联剂来限制 PX-PA 和 PX-PA-AEA 颗粒的溶胀。在所研究的三种微凝胶系统中,PVP-PA-AEA 具有高 AEA 掺入量和 pH 引发溶胀的最佳组合。 (C) 2013 作者。由爱思唯尔有限公司出版。保留所有权利。
In this study we introduce a general method for functionalising microgel particles with primary amine groups using a one-step copper catalysed azide-alkyne cycloaddition (CuAAC) reaction. Three different families of microgels containing copolymerised propargyl acrylate (PA) were prepared and then reacted with 2-azido-1-ethylamine (AEA) using CuAAC. The microgels contained poly(ethyl acrylate) (PEA), poly(2-vinylpyridine) (PVP) or poly(N-isopropylacrylamide) (PNP). The functionalisation of the microgels containing PA (i.e., PX-PA) by AEA to give primary amine functionalised particles (PX-PA-AEA) was assessed by elemental analysis and FTIR. The reaction of AEA with PA was quantitative for each of the PX-PA-AEA microgels (X = EA, VP and NP). The PX-PA-AEA systems generally showed larger pH-triggered swelling and zeta potentials than the non-clicked PX-PA particles. The results also showed that PA restricted swelling of the PX-PA and PX-PA-AEA particles by acting as a crosslinker. Of the three microgel systems studied, PVP-PA-AEA had the best combination of high AEA incorporation and pH-triggered swelling. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.