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Pathway Complexity Versus Hierarchical Self‐Assembly in N ‐Annulated Perylenes: Structural Effects in Seeded Supramolecular Polymerization
Author(s) -
Greciano Elisa E.,
Matarranz Beatriz,
Sánchez Luis
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201801575
Subject(s) - supramolecular chemistry , self assembly , alkoxy group , monomer , perylene , polymerization , chemistry , amide , stereochemistry , molecule , organic chemistry , polymer , alkyl
Abstract Studies were carried out on the hierarchical self‐assembly versus pathway complexity of N‐annulated perylenes 1 – 3 , which differ only in the nature of the linking groups connecting the perylene core and the side alkoxy chains. Despite the structural similarity, compounds 1 and 2 exhibit noticeable differences in their self‐assembly. Whereas 1 forms an off‐pathway aggregate I that converts over time (or by addition of seeds) into the thermodynamic, on‐pathway product, 2 undergoes a hierarchical process in which the kinetically trapped monomer species does not lead to a kinetically controlled supramolecular growth. Finally, compound 3 , which lacks the amide groups, is unable to self‐assemble under identical experimental conditions and highlights the key relevance of the amide groups and their position to govern the self‐assembly pathways.