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Tuning of Morphology by Chirality in Self‐Assembled Structures of Bis(Urea) Amphiphiles in Water
Author(s) -
Tosi Filippo,
Berrocal José Augusto,
Stuart Marc C. A.,
Wezenberg Sander J.,
Feringa Ben L.
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202003403
Subject(s) - circular dichroism , chirality (physics) , amphiphile , differential scanning calorimetry , mesoscopic physics , self assembly , vesicle , materials science , enantiomer , crystallography , urea , morphology (biology) , nanotechnology , chemical engineering , chemistry , membrane , stereochemistry , polymer , organic chemistry , copolymer , chiral symmetry breaking , physics , engineering , genetics , biology , quark , biochemistry , quantum mechanics , nambu–jona lasinio model , thermodynamics , composite material
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.