Partial fluorination overcomes herringbone crystal packing in small polycyclic aromatics

Org Lett. 2005 Mar 17;7(6):1067-8. doi: 10.1021/ol050019c.

Abstract

[structure: see text] We report the synthesis and characterization of partially fluorinated condensed tetracyclic aromatic compounds. Typical edge-to-face/herringbone packing of nonfluorinated analogues is replaced here by columnar stacks with disk planes orthogonal to the columnar axes. Enhanced pi-overlap results with overlaid electron-poor and -rich regions.