Flexible and rigid "chirally distorted" π-systems: binaphthyl conjugates as organic CPL-active chromophores.

The inclusion of high-performance dyes into chiral π-conjugated systems is an effective strategy for activating significant chiroptical properties. We report the preparation and characterization of configurationally stable, axially-chiral π-conjugated systems in which acridone or 2,5-diarylamino-terephthalate has been fused into the chiral scaffold of a 1,1'-binaphthyl moiety. The high-yielding synthesis afforded π-conjugated systems with characteristics essentially matching those of the parent dyes while introducing detectable CPL activity in solution.