The present work deals with the synthesis of polycyclic heteroaromatic hydrocarbons based on functionalization of halogenated pyridine derivatives. Various pyrrolo[1,2-a][1,6]naphthyridines, (benzo-)thieno[3,2-f]quinoline , (benzo-)thieno[3,2-f]isoquinoline and 5- and 6-azaindoles were successfully developed based on sequential site- and regioselective Pd-catalyzed C-C and C-N coupling reactions, alkyne carbonyl metathesis and Bronsted acid mediated cycloisomerization. Selected synthesized final products were studied using UV and fluorescence spectroscopy to determine the optical properties.<eng>