Competition and cooperation between steric hindrance and hydrogen bonding of supramolecular discs

Abstract

We previously reported supramolecular polymers formed by π–π stacking between disc-shaped hexamers (rosettes) of barbituric acid-functionalized π-conjugated molecules. Herein, we investigated the impact of amide-mediated hydrogen bonding along two types of polymer backbones formed by distinct stacking of rosettes. The stabilization of the hydrogen bonds strongly depends on the intrinsic stacking arrangement of rosettes, which competes with the amide hydrogen-bonding.