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Issue 24, 2013
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Versatile thiolated thermosensitive polymers synthesized by ATRP of MEO2MA and AcSEMA, a new methacrylic monomer with a protected thiol group

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Abstract

Herein, the synthesis of a new monomer containing a protected thiol group, 2-(acetylthio)ethyl methacrylate (AcSEMA), is introduced. The monomer has been copolymerized via atom transfer radical polymerization (ATRP) with 2-(2-methoxyethoxy)ethyl methacrylate (MEO2MA) to obtain a series of well-defined hidden-thiol functionalized thermosensitive polymers. The new system exhibits a sharp lower critical solubility temperature (LCST) and after hydrolysis of the acetyl group, the thiolated copolymers exhibit pH responsiveness. Moreover, to show the versatility of AcSEMA, P(MEO2MA-co-AcSEMA) copolymers were in situ hydrolyzed and modified by thiol-ene Michael addition with some acrylate compounds. The click reaction was successfully performed as revealed by NMR and the change in the LCST. We finally demonstrate that the addition of these polymer coatings onto gold nanoparticles (AuNPs) results in the formation of stable, colloidal thermosensitive polymer@AuNP complexes due to bridge formation between the thiol groups of AcSEMA and the metallic NP surfaces. The formation of temperature responsive polymer coated plasmonic nanoparticles shows the promise of P(MEO2MA-co-AcSEMA) copolymers for building multifunctional nanostructures for drug-delivery, diagnosis, tagging, catalysis and organic electronics systems.

Graphical abstract: Versatile thiolated thermosensitive polymers synthesized by ATRP of MEO2MA and AcSEMA, a new methacrylic monomer with a protected thiol group

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Publication details

The article was received on 13 Jun 2013, accepted on 12 Jul 2013 and first published on 12 Jul 2013


Article type: Paper
DOI: 10.1039/C3PY00773A
Citation: Polym. Chem., 2013,4, 5751-5759
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    Versatile thiolated thermosensitive polymers synthesized by ATRP of MEO2MA and AcSEMA, a new methacrylic monomer with a protected thiol group

    M. Liras, O. García, N. Guarrotxena, M. Palacios-Cuesta and I. Quijada-Garrido, Polym. Chem., 2013, 4, 5751
    DOI: 10.1039/C3PY00773A

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