Calicene is aromatic in the ground state and, due to its adaptive aromatic nature, exhibits a reversal of its dipole between the ground and lowest excited state. The push-pull substitution pattern proposed here counteracts the dipolar aromatic resonance structure of calicene, leading to a reduction of ground-state aromaticity (Figure ) and a reduction or reversal in the ground-state dipoles in the substituted compounds (grey in Figure ). The substituted compounds do not exhibit dipole reversal, and the excited (T1) state dipoles of the pull and push-pull compounds are much larger than in the bare compound (orange in Figure ). Thus, it can be understood that the CT-type states become the lowest excited states by virtue of the substituents counteracting the intrinsic dipole of the calicene motif. As a result, the ground-state aromaticity of the substituted compounds is attenuated relative to to bare calicene. Furthermore, the push-pull derivative is mildly Baird aromatic in both rings in the T1 state, unlike calicene and the push and pull derivatives (Figure ).