Novel chiral macrocycles containing two electronically interacting arylenechromophores

Novel chiral macrocycles consisting of two rigid oligoarylene rods and two chiral spiroindane clips have been synthesized by condensation of spiroinda ne diols and CF3-activated alpha-omega -difluorooligoaryls. Since a broad v ariety of planar aromatic macrocycles is known, our non-planar, chiral ring s represent a new crass of macrocyclic compounds. The first two examples, w hich contain quaterphenylene and diphenylbithiophene rods, are presented in this communication; for one of them a crystal structure is given. The chir optical properties of the macrocycles can be interpreted as an interplay of the "intrarod" helicity of individual oligoarylene rods and the "inter-rod " helicity between both chromophores of the macrocycle. The macrocycles can act as chiral dopands of commercially available, and novel, polymeric nema tic liquid crystals (emissive polyfluorenes). The "intra-rod" helicity of i ndividual oligoarylene rods is the main feature in determining the resultin g helical twisting power (HTP). The cholestric induction in mesogenic, emis sive polyfluorenes is of special interest for a realization of electronic d evices that have a circularly polarized electroluminescence. The results ar e also important for an understanding of larger ensembles of chiral rodlike molecules, especially their pi-pi interactions.