To further illustrate the robustness of our approach, we have calculated the X-CP-X and X-F6CP-X series with X = TNaph1, TNaph2, TAnt1, TAnt2, TAnt3. For the nonfluorinated backbone with both naphthalene side groups, the desired unoccupied orbital leading to photocyclization is the LUMO+2, which is notably stabilized (by ~1.2 eV) upon fluorination of the CP backbone and becomes the LUMO in TNaph1-F6CP-TNaph1 and TNaph2-F6CP-TNaph2. Therefore, our calculations show how photocyclization is strongly activated by fluorination, in accordance with experimental observations. In the anthracene series, fluorination also stabilizes the desired unoccupied molecular orbital, by ~1.10-1.30 eV, facilitating photocyclization. Still, such stabilization is not sufficient for the S1 state to become the one with the proper orbital occupation leading to the closed-form photoproduct. According to our calculations, a higher lying optically active excited state (S5) is responsible for the experimentally observed photocyclization of the fluorinated anthracene series. Our results are indicative that photocyclization will only occur if the excitation energy is high enough. Indeed, in these experiments, photocyclization was achieved by exciting at the high-energy tail of the lowest-energy absorption band. Therefore, in spite of the LUMO of X-F6CP-X with X = TAnt1, TAnt2, TAnt3 not having the expected π*-type interaction, our calculations are still consistent with the experimental results.