Issue 39, 2024

Core charge of imidazolium annulated triphenylene derivatives induces discotic columnar mesomorphism

Abstract

Thermotropic ionic liquid crystals have remained a relatively little studied group of materials despite their many potential applications as anisotropic ionic liquids and charge (ion and electron/hole) transporting materials. Particularly rare are core charged discotic liquid crystals because their synthesis is usually more involved, and their molecular design is less established. Presented here is a straightforward and versatile synthetic approach to imidazolium annulated triphenylene derivatives. Their neutral imidazole precursors are not liquid crystalline while the imidazolium salts display hexagonal discotic columnar mesophases over a wide range of temperatures and as low as 47 °C. Computational studies at the DFT and PM6 levels of theory confirmed much higher stacking energies for the imidazolium salts compared to the neutral imidazole precursors. They also predicted the anions of columnar stacks of imidazolium salts to be positioned in the bay-positions next to the imidazolium unit and in-plane with the polyaromatic system. The anions were stabilized in the bay position by multiple interactions with partially positively charged H atoms and do not interfere with π–π stacking.

Graphical abstract: Core charge of imidazolium annulated triphenylene derivatives induces discotic columnar mesomorphism

Supplementary files

Article information

Article type
Paper
Submitted
19 Jun 2024
Accepted
12 Sep 2024
First published
24 Sep 2024

Soft Matter, 2024,20, 7854-7864

Core charge of imidazolium annulated triphenylene derivatives induces discotic columnar mesomorphism

S. Chen, H. Taing, M. Ahmida, H. Y. He, A. Carr, H. M. Muchall and S. H. Eichhorn, Soft Matter, 2024, 20, 7854 DOI: 10.1039/D4SM00753K

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