Double Gyroid Nanostructure Formation by Aggregation-Induced Atropisomerization and Co-Assembly of Ionic Liquid-Crystalline Amphiphiles

Angewandte Chemie
Nanami UemuraTakahiro Ichikawa

Abstract

Herein we report a new molecular design principle for creating double gyroid nanostructured molecular assemblies based on atropisomerization. Ionic amphiphiles containing two imidazolium rings in close proximity to one another were designed and synthesized. NMR data revealed that the rotation of the imidazolium rings is restricted, with an activation energy as high as 63 kJ mol -1 in DMSO- d 6 solution. DFT calculations predicted an activation energy of 90-100 kJ mol -1 in vacuum for a model compound. Due to the restricted rotation, the amphiphiles feature "double" atropisomeric axes in their ionic segments and form three stable atropisomers, namely: meso, R and S . We found that these isomers co-organize into Ia Common.EditSubmissionSteps.Transform.EquationText d -type bicontinuous cubic liquid-crystalline mesophases through nanosegregation of the ionic and non-ionic parts, respectively. Considering the intrinsic characteristic of Ia Common.EditSubmissionSteps.Transform.EquationText d -type bicontinuous cubic structures that they are composed of intertwined, right- and left-handed single gyroids, we propose that the simultaneous presence of both R and S atropisomers is an important contributor to the formation of double gyroid...Continue Reading

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Citations

Mar 16, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Yan Yan LiXiao-Ping Zhou

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Methods Mentioned

BETA
NMR
differential
X‐ray

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