The future of next-generation electronics relies on low-cost organic semiconductors that are tailored to simultaneously provide all requisite optoelectronic properties, focusing greatly on ambipolar charge-transport and solution processability. In this regard, room-temperature discotic liquid crystals (DLCs) are potential candidates, where quasi-1D self-assembly affords a charge-transport channel along their columnar axis. This work shows a molecular design strategy by utilizing anthraquinone as the primary motif, surrounded by ester functionalized tri-alkoxy phenyl units to develop room-temperature DLCs (1.1-1.3). Here, the polar ester functionality stabilizes the columnar mesophase over a wide range through the involvement of dipole-dipole interaction along with the π-π stacking. Throughout the entire mesophase transition, reported compounds 1.1-1.3 exhibit a highly ordered 2D columnar oblique (Col