Issue 3, 2010

Self-assembly and hydrogelation promoted by F5-phenylalanine

Abstract

Phenylalanine (Phe)-derived molecules have been exploited as low molecular weight hydrogelators. Perturbing the hydrophobic and π–π interactions that promote self-assembly and hydrogelation of these derivatives will facilitate improved understanding of hydrogelation phenomena and the design of small molecule hydrogelators with novel properties. The efficient self-assembly and hydrogelation of Fmoc-protected pentafluorophenylalanine (Fmoc-F5-Phe) are reported herein. Suspensions of Fmoc-F5-Phe in water undergo rapid self-assembly to entangled fibrillar structures within minutes, giving rise to rigid supramolecular gels. Self-assembly occurs at concentrations as low as 2 mM (0.1 wt%). Variation of the fluorinated aromatic side chain or N-terminal functionalization perturbs hydrogelation, implicating fluorous and π–π interactions as the primary determinants for molecular recognition and self-assembly. The hydrophobic and electronic properties of F5-Phe provide remarkable potential for functional self-assembly in a minimal amino acid scaffold.

Graphical abstract: Self-assembly and hydrogelation promoted by F5-phenylalanine

Supplementary files

Article information

Article type
Communication
Submitted
13 Aug 2009
Accepted
10 Nov 2009
First published
01 Dec 2009

Soft Matter, 2010,6, 475-479

Self-assembly and hydrogelation promoted by F5-phenylalanine

D. M. Ryan, S. B. Anderson, F. T. Senguen, R. E. Youngman and B. L. Nilsson, Soft Matter, 2010, 6, 475 DOI: 10.1039/B916738B

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