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Double‐gyroid nanostructure formation by aggregation‐induced atropisomerization and co‐assembly of ionic liquid‐crystalline amphiphiles

DOI: 10.1002/anie.202000424 DOI Help

Authors: Nanami Uemura (Tokyo University of Agriculture and Technology) , Tsubasa Kobayashi (Tokyo University of Agriculture and Technology) , Shintaro Yoshida (Kitasato University) , Ya‐xin Li (University of Sheffield) , Karel Goossens (Institute for Basic Science (IBS), South Korea) , Xiangbing Zeng (University of Sheffield) , Go Watanabe (Kitasato University) , Takahiro Ichikawa (Tokyo University of Agriculture and Technology)
Co-authored by industrial partner: No

Type: Journal Paper
Journal: Angewandte Chemie International Edition , VOL 1

State: Published (Approved)
Published: March 2020
Diamond Proposal Number(s): 17966 , 18003

Open Access Open Access

Abstract: We report a new molecular‐design principle for creating double‐gyroid nanostructured molecular assemblies based on atropisomerization. Ionic amphiphiles containing two imidazolium rings close to each other 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‐d6 solution (DFT prediction for a model compound in the vacuum: 90–100 kJ mol−1). Due to the restricted rotation, the amphiphiles feature “double” atropisomeric axes in their ionic segments and form three stable atropisomers: meso, R, and S. These isomers co‐organize into urn:x-wiley:14337851:media:anie202000424:anie202000424-math-0001 ‐type bicontinuous cubic liquid‐crystalline mesophases through nanosegregation of the ionic and non‐ionic parts. Considering the intrinsic characteristic of urn:x-wiley:14337851:media:anie202000424:anie202000424-math-0002 ‐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 structures.

Journal Keywords: atropisomers; bicontinuous cubic phase; double-gyroid structures; liquid crystals; self-organization

Subject Areas: Chemistry

Instruments: I22-Small angle scattering & Diffraction

Added On: 23/04/2020 13:52


Discipline Tags:

Chemistry Chemical Engineering Engineering & Technology Organic Chemistry

Technical Tags:

Scattering Small Angle X-ray Scattering (SAXS)