Given their interest to supramolecular chemistry, several partially and fully fluorinated DBAs have been synthesized and their aggregation behavior has been studied through concentrationdependent NMR and UV-vis spectroscopy, vapor pressure osmometry (VPO), and single crystal X-ray diffraction (XRD). Shu and co-workers have shown that the favored fluoroarene-arene interactions led to the aggregation of a hexagonally shaped, partially fluorinated diyne-linked DBAs, evidence by the SEM images which showed the formation of rod-like crystallites with a hexagonal crosssection. However, most of these studies were performed on the sixor three-fold symmetric DBAs in which the arene and the fluoroarene components shared either an ortho or a meta substitution pattern. In this Letter, we present the synthesis and crystallographic characterization of two diamond-shaped partially fluorinated DBAs 1 and 2 (Scheme 1). These two macrocycles have two meta-connected arene and two ortho-connected tetrafluoroarene rings bridged by ethynylene moieties. Macrocycle 2 was synthesized to examine the influence of the exoannular substitution on the packing of the diamond-shaped macrocycle. Scheme 1. Syntheses of dehydrobenz [18]annulene macrocycles 1 and 2 via Sonogashira coupling.