Hydrogen-Bond Controlled π-Dimerization in Viologen-Appended Calixarenes: Revealing a Subtle Balance of Weak Interactions.
The intramolecular π-dimerization between two 4,4'-bipyridinium cation radicals directly connected to the wide rim of a calixarene is described. The ability of a phenol-containing calixarene to dimerize in its two-electron-reduced state depends on a subtle balance of weak interactions associated with hydrogen bond formation on the lower rim and orbital overlap between π-radicals on the upper rim.
†Laboratoire de Chimie (UMR 5182), École Normale Supérieure de Lyon/CNRS Université de Lyon 1, Lyon, France.
Christophe
C
Kahlfuss
‡Département de Chimie Moléculaire (UMR 5250), Université Joseph Fourier/CNRS, Grenoble, France.
Anne
A
Milet
§Institut de Chimie, UMR 7177 CNRS-Université de Strasbourg, 1 rue Blaise Pascal, 67008 Strasbourg cedex, France.
Jennifer
J
Wytko
§Institut de Chimie, UMR 7177 CNRS-Université de Strasbourg, 1 rue Blaise Pascal, 67008 Strasbourg cedex, France.
Jean
J
Weiss
‡Département de Chimie Moléculaire (UMR 5250), Université Joseph Fourier/CNRS, Grenoble, France.
Eric
E
Saint-Aman
†Laboratoire de Chimie (UMR 5182), École Normale Supérieure de Lyon/CNRS Université de Lyon 1, Lyon, France.
Christophe
C
Bucher