Helical Oligonaphthodioxepins Showing Intense Circularly Polarized Luminescence (CPL) in Solution and in the Solid State

A series of oligonaphthodioxepins was synthesized, revealing a helically arranged octamer, (R,R,R,R,R,R,R)-3, which showed intense circularly polarized luminescence (CPL) both in solution and in the solid state. The fluorescence quantum yields (ΦFL) in solution and in the solid state were 0.90 and 0.22, respectively, and the glum values in solution and in the solid state were +2.2 × 10-3 and +7.0 × 10-3, respectively. This is one of the highest solid-state CPL glum values yet reported. The high ΦFL and glum values were due to the rigidity as well as to the fact that (R,R,R,R,R,R,R)-3 was a non-planar molecule. Moreover, (R,R,R,R,R,R,R)-3 was highly stable both chemically and stereochemically.