Pathway Complexity Versus Hierarchical Self-Assembly in N-Annulated Perylenes: Structural Effects in Seeded Supramolecular Polymerization

Angewandte Chemie
Elisa E GrecianoLuis Sanchez

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.

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Citations

May 19, 2018·Chemical Communications : Chem Comm·Goutam Ghosh, Suhrit Ghosh
Nov 8, 2018·Angewandte Chemie·Jorge S ValeraLuis Sánchez
Mar 28, 2019·Chemistry : a European Journal·Soichiro OgiShigehiro Yamaguchi
Apr 16, 2019·Chemistry : a European Journal·Yongxian GuoYanke Che
Aug 6, 2019·Angewandte Chemie·Virgile AyzacLaurent Bouteiller
Jul 5, 2019·Angewandte Chemie·Jonas MaternGustavo Fernández
Oct 29, 2019·Chemistry : a European Journal·Manuel A MartínezLuis Sánchez
Dec 19, 2019·Angewandte Chemie·Ingo HelmersGustavo Fernández
Jul 28, 2019·Angewandte Chemie·Nils BäumerGustavo Fernández
May 29, 2020·Chemical Communications : Chem Comm·Goutam GhoshSuhrit Ghosh
Jul 9, 2020·Chemical Communications : Chem Comm·Ingo HelmersGustavo Fernández
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