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

doi:10.1002/chem.202003403

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^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

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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 language	English
Pages (from-to)	326-330
Number of pages	5
Journal	Chemistry
Volume	27
Issue number	1
Early online date	12-Aug-2020
DOIs	https://doi.org/10.1002/chem.202003403
Publication status	Published - 4-Jan-2021

Keywords

amphiphiles
bis(urea)
chirality
ribbons
self-assembly

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Tuning of Morphology by Chirality in Self‐Assembled Structures of Bis(Urea) Amphiphiles in WaterFinal publisher's version, 2.67 MBLicence: CC BY

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

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.",

keywords = "amphiphiles, bis(urea), chirality, ribbons, self-assembly",

author = "Filippo Tosi and Berrocal, {Jos{\'e} Augusto} and Stuart, {Marc C A} and Wezenberg, {Sander J} and Feringa, {Ben L}",

note = "{\textcopyright} 2020 Wiley-VCH GmbH.",

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T1 - Tuning of Morphology by Chirality in Self-Assembled Structures of Bis(Urea) Amphiphiles in Water

AU - Tosi, Filippo

AU - Berrocal, José Augusto

AU - Stuart, Marc C A

AU - Wezenberg, Sander J

AU - Feringa, Ben L

PY - 2021/1/4

Y1 - 2021/1/4

N2 - 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.

AB - 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.

KW - amphiphiles

KW - bis(urea)

KW - chirality

KW - ribbons

KW - self-assembly

U2 - 10.1002/chem.202003403

DO - 10.1002/chem.202003403

M3 - Article

C2 - 32785999

SN - 0947-6539

VL - 27

SP - 326

EP - 330

JO - Chemistry

JF - Chemistry

IS - 1

ER -

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

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