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N ‐Annulated Perylene Bisimides to Bias the Differentiation of Metastable Supramolecular Assemblies into J‐ and H‐Aggregates
Author(s) -
Greciano Elisa E.,
Calbo Joaquín,
Ortí Enrique,
Sánchez Luis
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202005837
Subject(s) - supramolecular chemistry , perylene , van der waals force , metastability , amide , chemistry , supramolecular polymers , dipole , stereochemistry , crystallography , molecule , organic chemistry , crystal structure
Abstract 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 rich differentiation that N ‐annulated PBIs exhibit, opening the door to new, complex, functional supramolecular materials.