A straightforward method for the synthesis of a series of hitherto unknown 1-azapyrenes is reported, which relies on a combination of Pd-catalyzed cross-coupling reactions with Brønsted acid-mediated cycloisomerization reactions. The methodology is highly modular and allows an efficient synthesis of various substituted products in high yields. The structural, electrochemical, and photophysical properties of 1-azapyrenes have been studied by ultraviolet-visible (UV-vis) and fluorescence spectroscopies, cyclic voltammetry, and density functional theory (DFT) calculations.