Although various perylene derivatives have been studied widely, circularly polarized luminescence (CPL) perylenes in the aggregated state are seldom presented due to the ACQ effect. In this study, a novel diphenylacrylonitrile–perylene derivative with peripheral chiral alkyl chains (CPL-P) was designed and prepared in 81% yield. CPL-P showed Col_h mesophase with a wide mesomorphic temperature ranging from 42.8 °C to 155.6 °C. Its photophysical studies suggested good fluorescence emission (550–700 nm) in the aggregated state due to the AIE-FRET effect between the diphenylacrylonitrile unit and perylene skeleton. The chiral optical investigation implied that CPL-P exhibited excellent CPL emission in the aggregated state, which could be attributed to the favourable influence of the AIE-FRET effect and the effective chiral transfer from chiral alkyl chains to the perylene skeleton based on the spiral columnar mesophase. This work not only presents a novel perylene derivative with a good CPL property in the aggregated state, but also opens a new strategy of combining the AIE-FRET effect and chiral transfer based on mesomorphic self-assembly to construct normal dye derivatives with excellent CPL property in the aggregated state.