Effect of chirality in the supramolecular polymerization of annulated perylenediimides: cancelling pathway complexity

Abstract

Herein, the synthesis of two chiral NPBIs, (S)-1 and (R)-1, is reported andtheir self-assembling features investigated. The reported NPBIs form chiralsupramolecular polymers with a rich dichroic pattern by the π-stacking of thearomatic backbones and the formation of an array of H-bonds between theamide functional groups. Furthermore, the peripheral 3,4,5-trialkoxy benza-mide groups can form seven-membered pseudocycles by the intramolecularH-bonding interaction between the NH of the peripheral amides and one ofthe carbonyls of the imide units thus yielding a kinetically controlled self-assembly process. Unlike achiral NPBI 1, that has been reported to form up tofour supramolecular polymorphs, the reported chiral NPBIs form only a J-typeaggregated species. The results presented herein reveal how subtle changesexert an enormous influence on the supramolecular polymerization outcome