Issue 7, 2022

Liquid-crystalline perylene bisimide derivatives bearing an azacrown ether ring complexing with alkaline metal ions

Abstract

For electrochemical applications, solution-processable redox-active materials with ion conductivity are required. Moreover, the thin films should be insolubilized for the usage with electrolyte solutions. We synthesized a perylene bisimide derivative bearing an azacrown ether moiety. The perylene bisimide derivative exhibited a rectangular ordered columnar phase at room temperature. This compound formed liquid crystalline complexes with lithium triflate and sodium triflate in a molar ratio of 1 : 1 while phase separation occurred in the mixture with potassium triflate in a molar ratio of 1 : 1. This liquid crystalline perylene bisimide derivative was soluble even in non-polar organic solvents, due to bulky cyclotetrasiloxane rings and thin films being produced by the spin-coating method. AFM studies revealed fibrous nanostructures on the surfaces of the films of the complexes, indicating the formation of supramolecular columnar structures. The spin-coated thin film of this compound could be insolubilized by an exposure on the vapors of trifluoromethanesulfonic acid via an in situ ring-opening polymerization process. The insolubilized thin film exhibited electrochromism between red neutral and violet dianion states.

Graphical abstract: Liquid-crystalline perylene bisimide derivatives bearing an azacrown ether ring complexing with alkaline metal ions

Supplementary files

Article information

Article type
Research Article
Submitted
22 Nov 2021
Accepted
18 Jan 2022
First published
19 Jan 2022

Mater. Chem. Front., 2022,6, 880-890

Liquid-crystalline perylene bisimide derivatives bearing an azacrown ether ring complexing with alkaline metal ions

T. Taga, S. Takaoka, S. Uemura and M. Funahashi, Mater. Chem. Front., 2022, 6, 880 DOI: 10.1039/D1QM01542G

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