All tetramers, hexamers, and octamers in this study were constructed from the dimer data set and are of the form (AB)n, where "(AB)n" is the alternating co-oligomer, "AB" is one of the 4095 dimer combinations, and "n" is the number of dimer repeat units. All 4095 tetramer combinations (n = 2) were included in the study. A random selection of 120 diverse dimer combinations was used to generate hexamer (n = 3) data, and 70 of these 120 combinations were randomly selected to generate octamer (n = 4) data. To ensure the small subset of compounds in the octamer set were representative of the entire data set, the distribution and range of the dimer HOMO/LUMO energies of the 120 combinations used to build hexamers and the 70 combinations used to build octamers were compared to the dimer energies of the entire data set. Figure of the supporting information contains a scatter plot illustrating this comparison. The dimer, tetramer, hexamer, and octamer energy data for the 70 combinations in the octamer subset were used to extrapolate the infinite polymer energy data for these 70 compounds. Only 60 of these 70 compounds were used to construct the predictive OLS models for the polymer energies. The remaining 10 compounds were used as a validation set.