Extreme Complementarity in a Macrocycle−Tweezer Complex

Interaction of a novel pyrene-based tweezer molecule with a macrocyclic ether-imide-sulfone results in formation of a strongly bound complex
(Ka = 24 000 M-1) in which binding results not only from π−π 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”
π-stacking of the electron-poor isophthaloyl residue of the tweezer with an electron-rich 3-aminophenoxy residue of the macrocyclic imide.