Stable radicals are challenging to prepare due to their intrinsic high reactivity.Herein,three trisphenolamine radicals were readily synthesized and exhibited unexpected thermal/electrochemical stability and semiconductor property.These three nitroxide radicals could be considered as a class of aromatized nitro groups or HNO3 derivatives.The closed-shell nitro-like and open-shell nitroxide resonance structure contribute to their outstanding stability.Furthermore,the tunable ground states,extremely low band gap and p-type charge transport properties were systematically investigated.More importantly,the work presents the concept of aromatic inorganic acid radical (AIAR) and aggregation-induced radical (AIR) mechanism to understand the intrinsic structureproperty relationship of these radicals.In addition,we provide a novel strategy for the design of stable and low bandgap radicals for organic electronics,magnetics,spintronics,etc.