Extreme complementarity in a macrocycle-tweezer complex

Colquhoun, H.M., Zhu, Z. and Williams, D.J. (2003) Extreme complementarity in a macrocycle-tweezer complex. Organic Letters, 5 (23). pp. 4353-4356. ISSN 1523-7060 doi: 10.1021/ol035626j

Abstract/Summary

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-(HO)-O-... and C-(HO)-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.