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Royal Society of Chemistry, Organic and Biomolecular Chemistry, 4(13), p. 1030-1039

DOI: 10.1039/c4ob02185a

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Tuning the pH-triggered self-assembly of dendritic peptide amphiphiles using fluorinated side chains

Journal article published in 2015 by Ralph Appel, Sebastian Tacke, Jürgen Klingauf, Pol Besenius ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

We report the synthesis of a series of anionic dendritic peptide amphiphiles of increasing hydrophobic character. By establishing state diagrams we describe their pH and ionic strength triggered self-assembly into supramolecular nanorods in water and highlight the impact of hydrophobic shielding in the supramolecular polymerisation process. Via the incorporation of fluorinated peptide side chains the pH-triggered monomer to polymer transition at physiological ionic strength is shifted from pH 5.0 to pH 7.4. We thereby show that by compensating attractive non-covalent interactions and hydrophobic effects with repulsive electrostatic forces, a concept we refer to as frustrated growth, is a sensitive tool in order to manipulate one-dimensional supramolecular polymerisation processes in water.