Exploring the functional potential of bent-core liquid crystal-based molecules with an amide linking group

Simic, Kristina Gak ; Ðordevic, Ivana ; Rybak, Paulina ; Pociecha, Damian ; Giménez, Raquel ; Ros, Maria Blanca (Universidad de Zaragoza) ; Trišovic, Nemanja

Resumen: A new series of bent-core molecules containing a photoactive π-conjugated structure (azobenzene, stilbene or cyanostilbene) linked to the central aromatic ring by an amide group was synthesized and characterized. Their liquid crystalline properties were analyzed in relation to the molecular structure and compared with amide-containing bent-core liquid crystals from the literature. Replacement of the azobenzene structure with a unit based on stilbene, either with or without a cyano substituent, accounted for the most significant differences in liquid crystalline behavior among the synthesized compounds. Azobenzene compound exhibited an enantiotropic B7-type phase, while (cyano)stilbene compounds formed a monotropic B1Rev phase. Cyanostilbene derivatives were fluorescent and showed aggregation-induced emission (AIE) enhancement. Furthermore, these compounds showed mechanofluorochromism, as observable emission changes in the solid state as a result of mechanical grinding. These changes turned to be reversible upon fuming with tetrahydrofuran vapor. Quantum-chemical calculations were employed to provide a detailed analysis of the most probable conformers, the impact of the cyano group orientation on the transverse and longitudinal components of the molecular dipole moment, and the electronic properties. The obtained results offer valuable molecular design guidelines for the development of new stimuli-responsive self-assembled materials.

Idioma: Inglés

DOI: 10.1016/j.molliq.2025.129175

Año: 2026

Publicado en: Journal of Molecular Liquids 444 (2026), 129175 [11 pp.]
ISSN: 0167-7322

Financiación: info:eu-repo/grantAgreement/ES/DGA/E47-23R
Financiación: info:eu-repo/grantAgreement/ES/MICINN-FEDER/PID2021-122882NB-I00
Financiación: info:eu-repo/grantAgreement/ES/MICIU/CEX2023-001286-S

Tipo y forma: Article (PostPrint)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)