Fluorenylmethoxycarbonyl (Fmoc)protected phenylalanine (Phe) derivatives have been exploited as low molecularweight hydrogelators driven by hydrophobic and p-p interactions. Perturbation of the hydrophobic and p-p interactions that promoteself-assembly and hydrogelation will facilitate improved understanding of thegelation phenomena. It was observed that perfluorination and monohalogenationof the phenyl side chain of Fmoc-Phe resulted in efficient assembly andsubsequent hydrogelation, relative to unsubstituted Fmoc-Phe. Inaddition, the position of the halogen substitution (ortho, meta, para) and the halogen itself (F, Cl, Br)exerted a strong influence on the self-assembly rate and bulk rheologicalproperties. Greater understanding ofthese structure-function relationships will aid in the development of novelmaterials and provide guidelines for the design of low molecular weightgelators.

Effects of halogenation on
the self-assembly and hydrogelation of a small molecule

240th National Meeting (2010)

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Effects of halogenation on the self-assembly and hydrogelation of a small molecule