A powerful demonstration of stacking is found in the buckycatcher. This molecular tweezer is based on two concave buckybowls with a perfect fit for one convex fullerene molecule. Complexation takes place simply by evaporating a toluene solution containing both compounds. In solution an association constant of 8600 M is measured based on changes in NMR chemical shifts.
Pi stacking is prevalent in protein crystal structures, and also contributes to the interactions between small molecules and proteins. As a result, pi–pi and cation–pi interactions are important factors in rational drug design. One example is the FDA-approved acetylcholinesterase (AChE) inhibitor tacrine which is used in the treatment of Alzheimer's disease. Tacrine is proposed to have a pi stacking interaction with the indolic ring of Trp84, and this interaction has been exploited in the rational design of novel AChE inhibitors.