Complementary Hydrogen Bonding Between a Clicked C₃‐Symmetric Triazole Derivative and Carboxylic Acids for Columnar Liquid‐Crystalline Assemblies

Abstract

Perfekt ergänzt: Eine Reihe discotischer H‐Brücken‐gebundener Komplexe wurde aus einem durch Klick‐Chemie hergestellten Triazolderivat mit C3‐Symmetrie und Carbonsäuren erhalten (siehe Bild; R1, R2=Alkylgruppen). Wegen ihrer ausgedehnten starren Kernstruktur konnten die supramolekularen Scheiben unter Bildung hexagonaler columnarer flüssigkristalliner Phasen aufeinander gestapelt werden.

Establishing the Ellipsoidal Geometry of a Benzoic Acid-Based Amphiphile via Dimer Switching: Insights from Intramolecular Rotation and Facial H-Bond Torsion

“…Benzoic acids received considerable attention as external structure directing agents, 8 supramolecular clips, 9 complementary H-bonded mesogenic discs, 10 molecular templates, 11,12 and model amphiphilic systems for Langmuir−Blodgett film fabrication. 13−15 They are known to crystallize as cyclic dimers when no other competing hydrogen bonds are present.…”

“…Benzoic acids received considerable attention as external structure directing agents, supramolecular clips, complementary H-bonded mesogenic discs, molecular templates, , and model amphiphilic systems for Langmuir–Blodgett film fabrication. − They are known to crystallize as cyclic dimers when no other competing hydrogen bonds are present. Although the catemeric motif is generally seen in carboxylic acids like formic acid, acetic acid, β-tetrolic acid, oxalic acid, and fumaric acid, it is reported that the dimer motif in benzoic acids is unfavorable compared to catemeric when bulky substituents are present …”

An Unusual Stacking Transformation in Liquid‐Crystalline Columnar Assemblies of Clicked Molecular Propellers with Tunable Light Emissions

“…On cooling from the isotropic liquid phase, the LC phase at 181 °C displayed a fan‐like texture, which is typically found in the columnar LC phase of discotic LCs (Figure 1 b). 17 On further cooling to the other LC phase at 159 °C, the fan‐like texture did not alter, instead persisting to room temperature (Figure 1 c). Only the texture color changed, which is due to some variations in the sample thickness as the temperature decreased.…”

Advances in Metal‐Free Heterocycle‐Based Columnar Liquid Crystals

“…In a subsequent publication, the same group prepared another series of C 3 -symmetric triazole compounds (113 a-c) from 1,3,5-tris(alkyl-1-H-1,2,3-triazol-4-yl)benzene (TTB) following a similar synthetic route. [107] The reaction of the triazole compounds with trioctyloxy benzoic acid (1:3 molar ratio) lead to the formation of supramolecular complexes 114 a-c through hydrogen-bonding interactions (Scheme 36). Hydrogen bonds are formed by one nitrogen atom of each triazole ring with the hydroxyl hydrogen of the carboxylic acid groups.…”