Issue 1, 2014
From the journal:

Polymer Chemistry

Facile synthesis of chain end functionalized polyethylenes via epoxide ring-opening and thiol–ene addition click chemistry†

Yongjie Zhang,ab   Huayi Li,*a   Jin-Yong Dong*a  and  Youliang Hua  

* Corresponding authors

a Beijing National Laboratory of Molecular Sciences, CAS Key Laboratory of Engineering Plastics, Joint Laboratory of Polymer Science and Materials, Institute of Chemistry, Chinese Academy of Sciences, Zhongguancun North First Street 2, 100190 Beijing, PR China
E-mail: lihuayi@iccas.ac.cn, jydong@iccas.ac.cn

b University of Chinese Academy of Sciences, No. 19A Yuquan Road, 100049 Beijing, PR China

Abstract

A wide range of low-molecular-weight, narrow-molecular-weight-distribution chain end functionalized polyethylenes (Cef-PEs), including hydroxyl-, amino-, carboxyl-, sulfo-, chloro-, azide- and trimethoxysilane-terminated polyethylenes, were synthesized under mild conditions via epoxide ring-opening and thiol–ene addition reactions with epoxy- and vinyl-terminated PEs as starting materials, respectively. The selectivities of the functionalizations were excellent. Similarly, amphiphilic polyethylene-block-poly(ethylene glycol) copolymer (PE-b-PEG) was prepared for the first time by simply treating epoxy terminated PE with hydroxyl terminated PEG and potassium hydroxide. A unique combination of primary (hindered-phenol) and secondary (thioester) antioxidants was introduced into the chain end of PE via successive thiol–ene addition and transesterification reactions. All Cef-PEs were characterized unambiguously by NMR, GPC, DSC and FTIR.

Graphical abstract: Facile synthesis of chain end functionalized polyethylenes via epoxide ring-opening and thiol–ene addition click chemistry

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Article information

DOI
https://doi.org/10.1039/C3PY00727H
Article type
Paper
Submitted
04 Jun 2013
Accepted
19 Jul 2013
First published
19 Jul 2013

Polym. Chem., 2014,5, 105-115

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Facile synthesis of chain end functionalized polyethylenes via epoxide ring-opening and thiol–ene addition click chemistry

Y. Zhang, H. Li, J. Dong and Y. Hu, Polym. Chem., 2014, 5, 105 DOI: 10.1039/C3PY00727H

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