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Updated: Jan 17, 2026
From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
Crystal Structure of Iodinated Mesoionic Triphenylthiazol-3-ium-4-olates: Combination of Stacking and Halogen Bonding
Shoji Matsumoto1,2, Shun Suzuki1, Motohiro Akazome1
1Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, 1-33 Yayoicho, Inage-ku, Chiba, 263-8522, Japan.
Abstract:
The crystal structures of triphenylthiazol-3-ium-4-olates substituted with iodine atoms on different phenyl rings are investigated. Analysis of single molecule crystal structures reveals consistent torsion angles across all compounds. Specifically, excellent planarity with the mesoionic ring is achieved when the phenyl ring at the 5-position enables effective conjugation with the enolate moiety. Three types of halogen interactions are identified depending on the iodine substituent position: CO···I, π-electron···I, and I···I interactions. All crystal structures exhibited columnar stacking arrangements. Density functional theory calculations show that stacking interactions provide greater energetic stabilization than halogen bonds. Additionally, the columnar stacking arrangement is influenced by the nature of the halogen bonding.
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