Substituents role in highly symmetrical 1,2,3-triazoles derivatives toward self-assembly of soft liquid crystals

Triazole bent-core mesogens based on symmetrical bent-shaped of two 1,2,3-triazole ring arms were synthesized and characterized. The the thermail stability of those new synthesised mesogens from the embient temperature to 215 degrees C giving mesogenic phase transitions over a wide temperature range is investigated. A study of different substituents located on the rigid bentcore was carried out for compact supramolecular innovated architectures which were produced by self-assembly of many triazoles soft crystals with a liquid crystals behaviour. The synthetic procedures, characterizations and polymorphism of four novel bent-core mesogens comprising symmetrical 1,2,3-triazole arms were demonstrated. The preparation process was carried out throughclick chemistry via Cu-catalyzed azide-alkyne cycloaddition of nitro- and alkyl-substituted aromatic azides with aromatic compounds, comprising terminal alkyne groups and long alkyl or alkoxy side-chains. The triazole derivatives were fully characterized by 1H/13C NMR, Fourier-transform infrared spectroscopy (FTIR) and elemental analysis. The mesophases and textures were examined by employing polarizing optical microscope (POM), differential scanning calorimetry (DSC) and X-ray Diffraction (XRD). The analogues with shorter alkoxy terminal substituents displayed higher mesomorphic properties with wide mesomorphic temperature ranges compared to analogues with shorter alkoxy terminals. The morphological characteristics of the self-assembled triazoles were investigated by scanning electron microscopy (SEM) which demonstrated arrangement of highly ordered columnar architectures. These orders were driven by layer to next layer adjacent influences and 7C-7C stacking. The effect of 1,2,3-triazole ring and length of terminal aliphatic chains on the liquid crystalline performance were discussed. Through an appropriate choice of lateral structures employing click chemistry, both transition temperature and mesophases ranging from isotropic to columnar or B1/B4-like supramolecular liquid crystalline aggregates can be tuned.

Automated summary

Triazole bent-core mesogens with symmetrical bent-shaped of two 1,2,3-triazole ring arms were synthesized and characterized. The thermal stability and mesomorphic phase transitions of these novel mesogens were studied, showing a wide temperature range. Different substituents on the bentcore were investigated, resulting in compact supramolecular structures formed by self-assembly. The synthesis, characterization, and polymorphism of the bent-core mesogens were demonstrated, using click chemistry to introduce various substituents. The liquid crystalline performance and morphological characteristics were analyzed, showing the potential for tunable transition temperature and mesophases by selecting lateral structures.