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Polymers 2015, 7(12), 2478-2493; doi:10.3390/polym7121526

Synthesis and Complexation of Well-Defined Labeled Poly(N,N-dimethylaminoethyl methacrylate)s (PDMAEMA)

1
Laboratory of Organic and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstr. 10, D-07743 Jena, Germany
2
Jena Center for Soft Matter (JCSM), Friedrich Schiller University Jena, Philosophenweg 7, D-07743 Jena, Germany
3
Laboratory of Chemistry and Biotechnic, Ilmenau University of Technology, Weimarer Str. 25, D-98684 Ilmenau, Germany
*
Author to whom correspondence should be addressed.
Academic Editor: Richard Hoogenboom
Received: 20 October 2015 / Revised: 19 November 2015 / Accepted: 23 November 2015 / Published: 27 November 2015
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Abstract

We present the synthesis and characterization of well-defined polycationic copolymers containing thiazole dyes in the side chain. Atom transfer radical polymerization (ATRP) was used for the copolymerization of 3-azidopropyl methacrylate (AzPMA) and N,N-dimethylaminoethyl methacrylate (DMAEMA) of different composition. Thiazole-based alkyne-functionalized dyes (e.g., 5-methyl-4-(prop-2-yn-1-yloxy)-2-(pyridin-2-yl)thiazole, (MPPT)) were afterwards covalently attached using copper catalyzed azide alkyne cycloadditions (CuAAC) reaching contents of up to 9 mol % dye. Subsequent quaternization of the tertiary nitrogen of DMAEMA with strong methylation agents (e.g., methyl iodide) led to permanently charged polyelectrolytes. The materials were characterized by size exclusion chromatography, as well as NMR- and UV/VIS-spectroscopy. Particular attention is paid to the spectroscopic properties of the dyes in the side chain upon environmental changes such as pH and salinity. We anticipate the application of such precisely functionalized polyelectrolytes as temperature- and pH-responsive sensors in biomedical applications, e.g., within interpolyelectrolyte complexes. Concerning the latter, first complex formation results are demonstrated. View Full-Text
Keywords: atom transfer radical polymerization; intense chromophore; micellar interpolyelectrolyte complexes; polyelectrolytes atom transfer radical polymerization; intense chromophore; micellar interpolyelectrolyte complexes; polyelectrolytes
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Billing, M.; Rudolph, T.; Täuscher, E.; Beckert, R.; Schacher, F.H. Synthesis and Complexation of Well-Defined Labeled Poly(N,N-dimethylaminoethyl methacrylate)s (PDMAEMA). Polymers 2015, 7, 2478-2493.

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