Substituted triphenylenes and similar discotic molecules have a strong tendency toward columnar organization. Nematic mesophases are much less commonly observed in discotic systems. We have demonstrated a general strategy whereby discotic triphenylenes can be twinned to form stable, boardlike materials that display only nematic mesophases. The dominant structural feature that leads to nematic behavior is an enforced void region in the center of the macrocycle that results from bridging through the triphenylene 3,6-positions. This precludes simple columnar assembly because it would lead to free space through the center of each stack. Selection of appropriate bridging units allows materials to be designed which combine molecular features, such as the optoelectronic properties of electron-rich triphenylenes and conjugated thiophene units, with the processability, self-healing, and alignment features inherent in nematic mesophases. In addition, communication across twinned structures can lead to additional enhancement of optoelectronic behavior. This is particularly apparent in fully conjugated, planar twin 12 which is formally expected to have some antiaromatic character. This character is manifested in its spectral properties, and particularly noteworthy is its strong, Stokes shifted emission at around 500 nm.