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Chemistry. 2010 Mar 8;16(10):3176-83. doi: 10.1002/chem.200902139.

Solvent-induced structural transition of self-assembled dipeptide: from organogels to microcrystals.

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Beijing National Laboratory for Molecular Sciences (BNLMS), Key Lab of Colloid and Interface Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.


Organogels that are self-assembled from simple peptide molecules are an interesting class of nano- and mesoscale soft matter with simplicity and functionality. Investigating the precise roles of the organic solvents and their effects on stabilization of the formed organogel is an important topic for the development of low-molecular-weight gelators. We report the structural transition of an organogel self-assembled from a single dipeptide building block, diphenylalanine (L-Phe-L-Phe, FF), in toluene into a flower-like microcrystal merely by introducing ethanol as a co-solvent; this provides deeper insights into the phase transition between mesostable gels and thermodynamically stable microcrystals. Multiple characterization techniques were used to reveal the transitions. The results indicate that there are different molecular-packing modes formed in the gels and in the microcrystals. Further studies show that the co-solvent, ethanol, which has a higher polarity than toluene, might be involved in the formation of hydrogen bonds during molecular self-assembly of the dipeptide in mixed solvents, thus leading to the transition of organogels into microcrystals. The structural transformation modulated by the co-solvent might have a potential implication in controllable molecular self-assembly.

[Indexed for MEDLINE]

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