Air stable diradicaloid polycyclic aromatic hydrocarbons (PAHs) materials possess unique electronic and magnetic properties for various applications. In general, it is required to elongate conjugated distances between two radicals center to improve the air stability, complexing the synthetic procedures. Herein, the chalcogen containing rubicenes (O-, S-, and Se-rubicenes) were systematically investigated to understand the chalcogen effects on their physicochemical properties. Impressively, these rubicenes presented unprecedented diradical characters within one simple benzene ring and excellent air stabilities. Their diradical characters are manifested by single-crystal X-ray studies, variable temperature-nuclear magnetic resonance