Trends in the relative energies and strain energies of the small double helicenes are identified.
Dispersion-corrected DFT is necessary to obtain proper geometries of the double helicenes.
The strain is largely localized to the shared naphthyl moiety.
NICS(0) values indicate a significant loss of aromaticity in the shared naphthyl moiety.
1H and 13C NMR chemical shifts are computed as aids in identifying these molecules.