Extreme Complementarity in a Macrocycle−Tweezer Complex

[reaction: see text] Interaction of a novel pyrene-based tweezer molecule with a macrocyclic ether-imide-sulfone results in formation of a strongly bound complex (K(a) = 24 000 M(-)(1)) in which binding results not only from pi-pi stacking interactions involving pyrene units as donors and macrocyclic naphthalene-tetracarboximide and biphenylenedisulfone groups as acceptors but also from N-H.O and C-H.O hydrogen bonds and from "reverse" pi-stacking of the electron-poor isophthaloyl residue of the tweezer with an electron-rich 3-aminophenoxy residue of the macrocyclic imide.