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

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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.

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Tosi, F., Berrocal, J. A., Stuart, M. C. A., Wezenberg, S. J., & Feringa, B. L. (2021). Tuning of Morphology by Chirality in Self-Assembled Structures of Bis(Urea) Amphiphiles in Water. Chemistry - A European Journal, 27(1), 326–330. https://doi.org/10.1002/chem.202003403

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