Penta- and Decafluorinated Dibenzalacetones: Synthesis, Crystal Structure, and Cocrystallization Experiments

The
nonfluorinated parent dibenzalacetone 1 as well
as the corresponding penta- (2) and decafluorinated (3) derivative compounds were prepared, crystallized, and subjected
to co-crystallization experiments. Only 3 yielded a 1:1
co-crystal with 1, while 2 did not form
co-crystals with either 1 or 3. Powder X-ray
diffraction patterns were determined to verify the co-crystallization
experiments. The influence of the fluorine on the molecular geometry
and crystal packing were studied and comparatively discussed. Conclusions
with reference to the priority of Ar···ArF contact modes in the crystalline packing being in competition with
other fluorine and non-fluorine involved supramolecular interactions
were drawn.