Chiral diphenylacrylonitrile-perylene liquid crystal with circularly polarized luminescence in aggregated state

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