Stable Electron Spin Pan on Aromatic Oxalic Acid Radical

Abstract

Comprehensive SummaryThe stability of organic radicals in ambient condition is important for their practical application. During the development of organic radical chemistry, the electron‐withdrawing and steric hindrance groups are usually introduced to improve the stability of radicals via reducing the reactivity of radicals with oxygen in air. Herein, the electron‐withdrawing carbonyl groups are introduced to construct a planar aromatic oxalic acid radical (IDF‐O8) with two‐dimensional electron spin pan structure. Interestingly, IDF‐O8 exhibited a low optical bandgap of 0.91 eV in film, however, the multiple quinone resonance structures between electron‐withdrawing ketone and phenol radicals contribute to the high stability of open‐shell radical IDF‐O8 without protection of large steric hindrance groups. Under the irradiation of 808 nm (1.2 W·cm–2), IDF‐O8 reaches 147 °C in powder state. This work provides an efficient synthesis route for the open‐shell electron spin pan system, which is different from the famous fullerene, carbon nanotube and graphene. The electron spin pan can be extended to spin tube or spin sphere system based on the design strategy of aromatic inorganic acid radicals in future.