Tuning of Morphology by Chirality in Self-Assembled Structures of Bis(Urea) Amphiphiles in Water

Filippo Tosi, José Augusto Berrocal, Marc C A Stuart, Sander J Wezenberg, Ben L Feringa

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Abstract

We present the synthesis and self-assembly of a chiral bis(urea) amphiphile and show that chirality offers a remarkable level of control towards different morphologies. Upon self-assembly in water, the molecular-scale chiral information is translated to the mesoscopic level. Both enantiomers of the amphiphile self-assemble into chiral twisted ribbons with opposite handedness, as supported by Cryo-TEM and circular dichroism (CD) measurements. The system presents thermo-responsive aggregation behavior and combined transmittance measurements, temperature-dependent UV, CD, TEM, and micro-differential scanning calorimetry (DSC) show that a ribbon-to-vesicles transition occurs upon heating. Remarkably, chirality allows easy control of morphology as the self-assembly into distinct aggregates can be tuned by varying the enantiomeric excess of the amphiphile, giving access to flat sheets, helical ribbons, and twisted ribbons.

Original languageEnglish
Pages (from-to)326-330
Number of pages5
JournalChemistry
Volume27
Issue number1
Early online date12-Aug-2020
DOIs
Publication statusPublished - 4-Jan-2021

Keywords

  • amphiphiles
  • bis(urea)
  • chirality
  • ribbons
  • self-assembly

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