"Bottom-up" self-assembly and "cold crystallization" of butterfly shaped tetrabenzofluorene molecules.

Butterfly-shaped tetrabenzo[a,c,g,i]fluorene (TBF)-based molecules (1 and 2) were designed, synthesized and well characterized using various spectroscopic techniques. The single crystal X-ray structure of 1 shows the presence of intermolecular 3-D π-π stacking interaction and unprecedented "cold crystallization" in polycyclic aromatic molecules. We report for the first time, the "bottom-up" self-assembly of TBF based organic molecules. The supramolecular studies reveal the formation of vesicles and cuboid-shaped nanocrystals in THF-water and toluene solution, respectively.