Heavy group 15 carbene-stabilized neutral radicals

Radical species contain an unpaired electron and are known for their intrinsic high reactivity. Methods to stabilize radicals generally involve the introduction of conjugated systems and sterically hindering environments, such as by incorporating singlet carbenes. For dipnictogen centered carbene-stabilized radicals, neutral dinitrogen1 and diphosphorus2 centered radicals have been reported for Carbene-Pn-Pn-Ar systems (Pn = pnictogen, Ar = aryl); however, neutral mixed pnictogen systems have yet to be described in this context. In this work, a series of [ArNP(Carbene)][OTf] salts will be prepared, utilizing carbenes with varying π-accepting properties, and these salts will be reduced to generate stable radicals. The following investigation will include alternating the position of the aryl group and carbene: Carbene=NP-Ar, to determine any stabilization effects. Subsequently, the investigation of heavier Group 15 radicals with the general framework, Carbene=NPn-Ar (Pn = Sb, Bi), will be conducted.