Extending the π-conjugation of chiral rotatable oligonaphthyl derivatives results in longer circularly polarised luminescence (CPL) wavelengths and increased unpolarised-photoluminescence (PL) quantum yields. The CPL was observed to shift to a significantly longer wavelength and the PL quantum yield was greatly improved when the number of naphthyl units was extended from two (dimer) to four (tetramer). On the other hand, the wavelength and quantum yield increased less in moving from the tetramer to the octamer in solution and solid films.