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Updated: Jul 9, 2026
From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
Weak interactions defining the crystal packing in the sterically demanding compound
Armando Ferrer1,2, Yonatan Mederos1, Julio A Rojas Vargas3
1Departamento de Química, Facultad de Ciencias Naturales y Exactas, Universidad de Oriente - Santiago de Cuba, Av. Patricio Lumumba S/N, Santiago de Cuba, 90200, Cuba.
Abstract:
The synthesis of 1-(3-methylphenyl)-2-(4-nitrophenyl)-4,5-diphenyl-1H-imidazole, C28H21N3O2, has been efficiently achieved in a one-pot procedure from simple materials. Its structure was analysed with the help of a full set of spectroscopic techniques, X-ray crystallographic studies and computational calculations, suggesting that the compound shows some potential for being used in nonlinear optical (NLO) devices. Despite being a sterically demanding tetrasubstituted imidazole, this compound can form a stable crystal structure based on the combination of a large set of weak interactions. With four aryl substituents, displaced and tilted edge-to-face and face-to-face aromatic-aromatic interactions are responsible of many of the short contacts identified, representing the major contribution as determined with the use of Hirshfeld surfaces. The nitro groups also play a key role, being responsible of the polarization of the molecule with the formation of antiparallel assemblies, leading to well-defined stacks. Antiparallel N...O pairs are also present at relatively short distances, together with short H...O contacts (16.9% contribution), indicating the presence of weak hydrogen bonds of the O atoms with weakly acidic H atoms in the polarized structure.
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