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Different building blocks in organic molecules could induce complex intermolecular interactions to lead to different supramolecular micro/nanostructures in bulk and solution states. Herein, the first new phenolphthalein-based hexacatenar containing a central phenolphthalein fluorochrome functionalized with two dendritic wings is synthesized by click reaction. The polarized optical microscopy, differential scanning calorimetry, and small-angle X-ray diffraction data demonstrated that the reported phenolphthalein-based hexacatenar could self-assemble into hexagonal columnar mesophase in the bulk state and could form organogel with distinct morphologies in some common organic solvents due to intermolecular interactions. Density functional theory calculation results showed highly twisted molecular conformation, distinct charge distribution, and asymmetrical electronic property, which might be essential for the stabilization of columnar mesophase and organogel. Therefore, this work provides a method to develop soft materials containing different functional building blocks with complex self-assemblies.

Synthesis, liquid crystalline self-assembly, organogel behavior, and DFT investigation of first phenolphthalein-based hexacatenar