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

Arda Alkan, Laura Thomi, Tassilo Gleede, Frederik R. Wurm*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

20 Citations (Scopus)
4 Downloads (Pure)

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 (D ≤ 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.

Original languageEnglish
Pages (from-to)3617-3624
Number of pages8
JournalPolymer chemistry
Volume6
Issue number19
DOIs
Publication statusPublished - 21 May 2015
Externally publishedYes

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