Mixing the liquids hexafluorobenzene
(1) and 1,3,5-trimethylbenzene
(mesitylene, 2) results in a crystalline solid with a
melting point of 34 °C. The solid consists of alternating π–π
stacked pillars of both aromatics. This simple experiment can be used
to visually demonstrate the existence and the effect of noncovalent
intermolecular π–π stacking interactions. Both
benzene derivatives are relatively benign and widely available, and
the experiment can be performed within minutes for less than $15 when
done on a 22 mL scale (total volume). The demonstration is very robust,
as 1:2 mixtures in volume ratios between
2/3 and 3/2 all give a visually similar result (molar ratios of 1.8–0.8).
Substituting 2 with the liquid aromatics o-xylene, p-xylene, and aniline also resulted in
the formation of a crystalline solid, while using many other liquid
aromatics did not.