Using computational studies to explore the polymorphic landscapes of organic electronics helps improve our understanding of the underlying factors driving the packing behaviour and can direct electronic molecular materials design. In this study, our main focus was on the influence of n on the extent of π -π stacking interactions. We found that π -π interactions tend to dominate in high energy crystals, apart from when n = 5 -7 where there is little to no correlation, with a minimum when n = 6. As a high degree of π -π stacking can give rise to improved charge-transport properties, this result suggests that [5]- [7]helicene and their derivatives may be a fruitful avenue of exploration for developing functional organic electronics. This observation is further supported by the observation of chiral columns predominant in derivatives of either [6] or [7]helicene. π -π interactions are not the only motifs that result in favourable charge-transport properties, as evidenced by Rice et al. for [6]helicene; as such, future work on fully analysing the charge-transport properties of structures in each of the CSP landscapes reported here would be beneficial to develop further understanding of structure-property relationships in organic electronics.