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Issue 11, 2013
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pH degradable dendron-functionalized poly(2-ethyl-2-oxazoline) prepared by a cascade “double-click” reaction

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Abstract

In this study, we report on the synthesis of a dendron-functionalized poly(2-ethyl-2-oxazoline) in a one-pot cascade reaction approach. By means of a bifunctional small organic compound linker, namely (9-azidomethyl)anthracene, alkyne-functionalized PEtOx and maleimide-substituted dendron were coupled in a one-pot cascade approach exploiting the copper-catalyzed azide-alkyne cycloaddition (CuAAC) and the Diels–Alder cycloaddition. The resulting amphiphilic block copolymer was characterized by size-exclusion chromatography (SEC), proton nuclear magnetic resonance (1H NMR) spectroscopy and matrix-assisted laser desorption ionization time-of-flight (MALDI TOF) mass spectrometry (MS). Since the dendron contains acid-labile acetal protecting groups, it is pH responsive and the hydrophilicity significantly increases upon hydrolysis. The aqueous solution behavior and pH-responsivity of the PEtOx–dendron are discussed at neutral pH as well as acidic pH based on dynamic light scattering and fluorescence spectroscopy.

Graphical abstract: pH degradable dendron-functionalized poly(2-ethyl-2-oxazoline) prepared by a cascade “double-click” reaction

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Article information


Submitted
21 Feb 2013
Accepted
14 Mar 2013
First published
15 Mar 2013

Polym. Chem., 2013,4, 3236-3244
Article type
Paper

pH degradable dendron-functionalized poly(2-ethyl-2-oxazoline) prepared by a cascade “double-click” reaction

K. Kempe, S. Onbulak, U. S. Schubert, A. Sanyal and R. Hoogenboom, Polym. Chem., 2013, 4, 3236
DOI: 10.1039/C3PY00258F

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