B,N-doped organic analogues can be widely used in photoelectronic materials, medicine and other fields. However, B,N-doped cyclo[n]carbons have not yet been developed. Herein, we report a systematic investigation of the thermodynamic stability and aromaticity of mono B,N-doped cyclo[10]carbon isomers via density functional theory (DFT). Several rules for thermodynamic stability have been proposed. Specifically, rule 1: isomers with B,N atoms separated by an even number of C atoms are more stable than those separated by an odd number of C atoms.

Discovery of species with adaptive aromaticity (being aromatic in both the lowest singlet and triplet states) is particularly challenging as cyclic species are generally aromatic either in the ground state or in the excited state only according to Hückel’s and Baird’s rules.