A series of silacyclophanes with two carbazole units linked by two disilanyl pillars were synthesized by a concise one-pot procedure. The step-like structure of disilanyl double-pillared biscarbazole ((DPBC)-D-Si) in crystals was disclosed by X-ray diffraction analysis. In the solution phase, (DPBC)-D-Si fluctuated its structure rapidly on the NMR time scale with the aid of the wide-open angles of the two pillars, which was not observed with other congeners possessing tricyclic aromatic units.