The approach described here for n,* states of heteroaromatics can be generalized to analyze the aromaticity of other types of states with an odd total number of -electrons. It can be utilized to understand the (anti)aromatic character of metallaaromatics which are not only aromatic in S0 but also in their triplet * and * states, earlier labelled as adaptive aromatic. Our analysis can also be extended to π-conjugated radical anions and cations such as C6H6 + or C8H8 -with an even number of π-electrons and an odd number of π-electrons, or vice versa. Indeed, radical cations or anions were analyzed by Mandado and co-workers who found by spin-separated NICS that their π-component were antiaromatic and the πcomponents aromatic. Although the findings are fundamental in character, they can be applied. Earlier we found that amiloride-type drugs with central pyrazine moieties photodegrade along a two-step mechanism where the second step is a photoionization with an electron ejected from the antiaromatic T1 state of * character. By knowing that the energetic order between the n,* and * states of pyrazines switch with substituents, and that the n,* states have aromatic (stabilized) character, one may tailor amiloride-like compounds which have n,* states as their T1 states. Moreover, with knowledge on how to rationally tune the order between the lowest n,* and * states through substituents, it also becomes clear how to design quinoxolines with lowest n,* states, a feature that should be useful for design of targeted species with interesting emission properties.