A series of selenium-bridged and tellurium-bridged heteromerousbistricyclicaromaticenes (BAEs) 15–25 with six-member and seven-member central rings have been synthesized by Barton–Kellogg olefination, twofold extrusion coupling method between tricyclic aromatic thiones and tricyclic aromatic diazo derivatives. The crystal structures of thioxanthenylidene-anthracenone (15), selenoxanthenylidene-anthracenone