Inversion of Supramolecular Chirality by Sonication-Induced Organogelation

Sibaprasad Maity, Priyadip Das, Meital Reches*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

29 Scopus citations


Natural helical structures have inspired the formation of well-ordered peptide-based chiral nanostructures in vitro. These structures have drawn much attention owing to their diverse applications in the area of asymmetric catalysts, chiral photonic materials, and nanoplasmonics. The self-assembly of two enantiomeric fluorinated aromatic dipeptides into ordered chiral fibrillar nanostructures upon sonication is described. These fibrils form organogels. Our results clearly indicate that fluorine-fluorine interactions play an important role in self-assembly. Circular dichroism analysis revealed that both peptides (peptides 1 and 2), containing two fluorines, depicted opposite cotton effects in their monomeric form compared with their aggregated form. This shows that supramolecular chirality inversion took place during the stimuli-responsive self-aggregation process. Conversely, peptide 3, containing one fluorine, did not exhibit chirality inversion in sonication-induced organogelation. Therefore, our results clearly indicate that fluorination plays an important role in the organogelation process of these aromatic dipeptides. Our findings may have broad implications regarding the design of chiral nanostructures for possible applications such as chiroptical switches, asymmetric catalysis, and chiral recognitions.

Original languageAmerican English
Article number16365
JournalScientific Reports
StatePublished - 10 Nov 2015

Bibliographical note

Funding Information:
This work was supported by the EP7 Marie Curie International Reintegration Grant. S.M. and P.D. acknowledge the support of the Council for Higher Education in Israel. We thank Ms. Chen Nowogrodski and Prof. Daniel Cohn.

Publisher Copyright:
© 2015 Macmillan Publishers Limited.


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