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

Tosi, F., Berrocal, J. A., Stuart, M. C. A., Wezenberg, S. J. & Feringa, B. L., 12-Aug-2020, In : Chemistry.

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DOI

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 CD measurements. The system presents thermo-responsive aggregation behaviour and combined transmittance measurements, temperature dependent UV, CD, TEM and micro-DSC show that a ribbon-to-vesicles transition occurs upon heating. Remarkable, 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
JournalChemistry
Publication statusE-pub ahead of print - 12-Aug-2020

ID: 131526904