A number of electron-withdrawing and -donating substituents were tested at the at the R1 and R2 positions, respectively. We find that the Hund's rule violations are robust with various substituents (Figure and Table ), but note that only the strongest donating and withdrawing groups which remain in the plane of the calicene rings are sufficient to maintain the inversion between the S1 and T1 states at the EOM-CCSD level. However, the specific order of the states in the triplet manifold is method-dependent; with the CC2 method we find that more inversions are potentially between the S1 and T1 states than the EOM-CCSD computations suggest.