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Herein, we report the syntheses and characterization of liquid-crystalline (LC) 5,6,13,14-tetraazapentacene (BTANC) derivatives. A LC BTANC derivative self-organized to form a layered smectic A LC phase over a wide temperature range, including room temperature. Cyclic voltammetry of the LC BTANC derivate showed a reversible two-step and two-electron transfer in the reduction region. To the best of our knowledge, this is the first report on the derivatives of LC BTANC.

We report an introduction of halogen atoms to liquid‐crystalline (LC) TANC derivatives to tune their electronic characters as well as the charge polarization on π‐conjugated N‐heteroacene framework. The electronegative Cl atoms can improve the electron‐accepting property of LC TANC. Also, the induced charge polarization due to the substitution of Cl atoms generates an intrinsic dipole moment on π‐conjugated N‐heteroacene framework, which is able to serve as a driving force for stabilizing self‐organization of N‐heteroacene molecules in thin films.