Innenrücktitelbild: N ‐Annulated Perylene Bisimides to Bias the Differentiation of Metastable Supramolecular Assemblies into J‐ and H‐Aggregates (Angew. Chem. 40/2020)

Decoding the Consequences of Increasing the Size of Self-Assembling Tricarboxamides on Chiral Amplification

A complete series of experimental and theoretical investigations on the supramolecular polymerization of chiral (1 and 2) and achiral (3) oligo(phenylene ethynylene) tricarboxamides (OPE-TAs) is reported. The performance of seargents-and-soldiers (SaS) and majority rules (MR) experiments has allowed deriving a full set of thermodynamic parameters, including the helix reversal penalty (HRP) and the mismatch penalty (MMP). The results described illustrate the influence exerted by the number of stereogenic centers per monomeric unit and the temperature on the chiral amplification phenomenon. While the HRP decreases upon decreasing the number of chiral side chains, the MMP follows an opposite t…

N ‐Annulated Perylene Bisimides to Bias the Differentiation of Metastable Supramolecular Assemblies into J‐ and H‐Aggregates

The unique self-assembling features of N-annulated perylene bisimides (PBIs) 1 and 2 are reported. The stability of the aggregates of diester 1, in which no H-bonding interactions are operative, corroborates the significance of long-range van der Waals and dipole-dipole electrostatic interactions in the construction of stable supramolecular assemblies. The incorporation of amide functional groups within the N-annulated PBI in 2 stimulates pathway differentiation to achieve up to three J-type aggregates and a fourth H-type aggregate depending on the experimental conditions. The results presented demonstrate unprecedented levels of control over synthetic supramolecular self-assembly and the r…

Inside Back Cover: N ‐Annulated Perylene Bisimides to Bias the Differentiation of Metastable Supramolecular Assemblies into J‐ and H‐Aggregates (Angew. Chem. Int. Ed. 40/2020)