Co-Crystal Formation of Partially Fluorinated 1,3,5-Tris(phenylethynyl)benzenes

Several rigid 1,3,5-tris(phenylethynyl)benzenes with different fluorination patterns were synthesized through selective Sonogashira-Hagihara coupling reactions to analyze the packing behavior in solid-state structures. The aggregation is dominated by various intermolecular interactions between aryl substituents, triple bonds, C-H bonds and H...F contacts. Co-crystallization experiments for the analysis of preferred aryl-aryl-interactions led to 1 : 1 complexes. Intermolecular phenyl-perfluorophenyl interactions with short centroid-centroid distances are dominating these co-crystal structures. They lead to melting point increases of up to 49 degrees C for the co-crystals compared to the pure substances.

Automated summary

Synthesizing rigid benzenes with different fluorination patterns and analyzing their packing behavior in solid-state structures, it was found that intermolecular interactions can influence properties of co-crystal structures, such as melting points.