We report the synthesis of pyrrolo[3',2':3,4]fluoreno[9,1-]quinoline and pyrrolo[2',3',4':4,10]anthra[1,9-]quinoline derivatives. This novel class of N-doped polycyclic heteroaromatic compounds was synthesized by a site-selective cross-coupling reaction followed by acid-mediated cycloisomerization and Pd-catalyzed CH arylation as the final ring-closing reactions. Preliminary optical and aromatic properties were studied by means of steady-state absorption and fluorescence spectroscopy and DFT calculation. Special emphasis was placed on the impact of ring alternation and position of the N-doping within the scaffold.