Synthesis of Tetraaryl Diazachrysenes by the Povarov Reaction and π Extension To Construct a Condensed Azaperylene Motif

Abstract

Incorporating nitrogen into carbon‐based materials can significantly modify their electronic properties. A comprehensive understanding of the structural and physical characteristics of aza‐polycyclic aromatic hydrocarbons (aza‐PAHs) is crucial for developing innovative materials. In this study, four aza‐PAHs were synthesized using a combination of the Povarov reaction and intramolecular cyclization reaction by direct C−H arylation. The synthesized compounds were evaluated in terms of the crystal structure, photophysical properties, frontier energy levels, and hole‐blocking properties in organic light‐emitting diode (OLED). The intramolecular cyclization by direct C−H arylation afforded a condensed azaperylene molecule that exhibited long‐wavelength absorption and emission, attributed to the high HOMO level resulting from π‐extension.