Theoretical calculations (B3LYP-6-31G(d,p)) based on hypothetical homodesmotic reactions predict that the total strain is about 68.2 kcal/mol for the precursor 2a/2b, while around 103.9 kcal/mol for the fully conjugated MCNB 1 (Fig. in Supplementary Information). The much smaller strain energy in 2a/2b as compared to 1 indicates that the introduction of the THBT unit containing saturated -CH2-CH2-moieties is crucial for the successful cyclization reaction. The increased strain energy in the last oxidative dehydrogenative step can be partially compensated by the gained aromatic stabilization energy. In addition, the average strain energy for each twist in the triply twisted MCNB 1 is around 34.6 kcal/mol, which is smaller than that in the singly twisted (25,25)MCNB (49.4 kcal/mol). Moreover, the strain could be visualized along the molecular backbone through StrainViz developed by Jasti and co-workers. As shown in Fig. and Fig. , the total strain energy of 2a/2b is calculated as 110.8 kcal/mol, while the maximum strain energy of an individual bond is 1.9 kcal/mol. The corresponding strain energies of 1 also increase to 142.3 kcal/mol and 2.4 kcal/mol, respectively (Fig. ). Most of the strains for both 2a/2b and 1 are vastly located on the twist positions along the inner rims (Fig. ).