7:8,9:10-dibenzo-1,2,3,4-tetrafluoro- triphenylene: synthesis, structure, and photophysical properties of a novel [5]helicene.

A simple and efficient synthesis and crystallographic analysis of the partially fluorinated 7:8,9:10-dibenzo-1,2,3,4-tetrafluorotriphenylene, 1, in 59% yield is reported. Compound 1 is a blue luminescent [5]helicene in both solution and the solid state. It spontaneously forms enantiomorphous single crystals from racemic samples and exhibits slipped, face-to-face F...C(pi) contacts within the stacks of molecules.