Issue 19, 2015

Vinyl ferrocenyl glycidyl ether: an unprotected orthogonal ferrocene monomer for anionic and radical polymerization

Abstract

The first orthogonal ferrocene monomer, vinyl ferrocenyl glycidyl ether (VfcGE), for both anionic and radical polymerization – without the need of a protection group – is presented. Anionic ring-opening copolymerization of VfcGE and ethylene oxide (EO) generates stimuli-responsive, multifunctional poly[(vinyl ferrocenyl glycidyl ether)-co-(ethylene oxide)] (P[VfcGE-co-EO]) copolymers (molecular weights of ca. 7500 g mol−1 and low molecular weight dispersities (Đ ≤ 1.14)). The amount of the equimolar ferrocenyl and vinyl groups are controlled by the comonomer ratio up to 15.4 mol% VfcGE. The pendant vinyl groups of P[VfcGE-co-EO] were post-modified with 3-mercaptopropionic acid via thiol–ene chemistry. The EO copolymers exhibit temperature-, redox-, and pH-responsive behavior in water depending on the polymers’ microstructure. Free radical polymerization of VfcGE leads to polyalkylene:(vinyl ferrocenyl glycidyl ether) with pendant epoxide side chains at each ferrocene unit. The resulting polymer was used to generate redox-responsive protein nanoparticles with bovine serum albumin (BSA) by nucleophilic ring-opening of the pendant epoxides.

Graphical abstract: Vinyl ferrocenyl glycidyl ether: an unprotected orthogonal ferrocene monomer for anionic and radical polymerization

Supplementary files

Article information

Article type
Paper
Submitted
19 Mar 2015
Accepted
30 Mar 2015
First published
01 Apr 2015
This article is Open Access
Creative Commons BY license

Polym. Chem., 2015,6, 3617-3624

Author version available

Vinyl ferrocenyl glycidyl ether: an unprotected orthogonal ferrocene monomer for anionic and radical polymerization

A. Alkan, L. Thomi, T. Gleede and F. R. Wurm, Polym. Chem., 2015, 6, 3617 DOI: 10.1039/C5PY00404G

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