Compact and simple nondiscoid mesogens, trialkoxybenzoic anhydrides 2-11 ((RO)(3)C6H2CO-O-CO-C6H2(OR)(3), R = C2H5, n-C3H7, n-C4H9, n-C6H13, n-C8H17, n-C10H21, n-C12H25, n-C14H29, n-C16H33, and (S)- and (R)-3,7-dimethyloctyl) were designed and synthesized, and their superstructures were investigated by polarized light microscopy, differential scanning calorimetry, calculation (MM2 and AM1), circular dichroism spectroscopy, and X-ray diffraction. As the result, in the cases of 5-9 and 11, the half-disk molecules in the liquid crystal phases were self-assembled by the dipole-dipole interaction between their carbonyl groups to a column in which the molecules were piled up in an alternately antiparallel manner, and the columns were interdigitated each other. The observed interdigitations were highly directional in the perpendicular direction to the column axis. In the case of compound 11 which has (S)- or (R)-3,7-dimethyloctyl groups, a helical organization of the molecules in the column was estimated from the peaks in the circular dichroism spectra. This is the first report of a one-directionally interdigitated columnar phase, and these compounds are the first liquid crystalline acid anhydrides. It was demonstrated that a -CO-O-CO- moiety is useful as a polar junction in liquid crystalline compounds.