Chalcogen-substituted π-extended indolocarbazoles were synthesized through a nucleophilic cyclization of tethered diynes with sulfur, selenium or tellurium sources, followed by a Pictet–Spengler reaction. These combined synthetic strategies enabled the facile access to heptacyclic π-extended molecules, offering a broad modularity at various stages of the synthesis route. In total, twenty-six novel heptacyclic compounds were synthesized. Their photophysical and structural properties were investigated experimentally as well as theoretically.