We report a semiconducting triindole-based discotic liquid crystal () functionalized with six -methylthiophenyl groups at its periphery. While initially a crystalline solid at room temperature, transitions to a columnar hexagonal mesophase upon heating and retains this supramolecular organization upon subsequent cooling, despite having only three flexible alkyl chains attached to the core's nitrogens. The incorporation of methylthio groups effectively hinders tight molecular packing, stabilizing the columnar arrangement of this disk-shaped molecule.
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