Self‐Sorting Supramolecular Polymerization: Helical and Lamellar Aggregates of Tetra‐Bay‐Acyloxy Perylene Bisimide

Please always quote using this URN: urn:nbn:de:bvb:20-opus-224586
  • A new perylene bisimide (PBI), with a fluorescence quantum yield up to unity, self‐assembles into two polymorphic supramolecular polymers. This PBI bears four solubilizing acyloxy substituents at the bay positions and is unsubstituted at the imide position, thereby allowing hydrogen‐bond‐directed self‐assembly in nonpolar solvents. The formation of the polymorphs is controlled by the cooling rate of hot monomer solutions. They show distinctive absorption profiles and morphologies and can be isolated in different polymorphic liquid‐crystallineA new perylene bisimide (PBI), with a fluorescence quantum yield up to unity, self‐assembles into two polymorphic supramolecular polymers. This PBI bears four solubilizing acyloxy substituents at the bay positions and is unsubstituted at the imide position, thereby allowing hydrogen‐bond‐directed self‐assembly in nonpolar solvents. The formation of the polymorphs is controlled by the cooling rate of hot monomer solutions. They show distinctive absorption profiles and morphologies and can be isolated in different polymorphic liquid‐crystalline states. The interchromophoric arrangement causing the spectral features was elucidated, revealing the formation of columnar and lamellar phases, which are formed by either homo‐ or heterochiral self‐assembly, respectively, of the atropoenantiomeric PBIs. Kinetic studies reveal a narcissistic self‐sorting process upon fast cooling, and that the transformation into the heterochiral (racemic) sheetlike self‐assemblies proceeds by dissociation via the monomeric state.show moreshow less

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Metadaten
Author: Markus Hecht, Pawaret Leowanawat, Tabea Gerlach, Vladimir Stepanenko, Matthias Stolte, Matthias Lehmann, Frank WürthnerORCiDGND
URN:urn:nbn:de:bvb:20-opus-224586
Document Type:Journal article
Faculties:Fakultät für Chemie und Pharmazie / Institut für Organische Chemie
Language:English
Parent Title (English):Angewandte Chemie International Edition
Year of Completion:2020
Volume:59
Issue:39
First Page:17084
Last Page:17090
Source:Angewandte Chemie International Edition 2020, 59(39):17084–17090. DOI: 10.1002/anie.202006744
DOI:https://doi.org/10.1002/anie.202006744
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Tag:liquid crystals; noncovalent interactions; self-assembly; structure elucidation; supramolecular chemistry
Release Date:2021/10/28
Licence (German):License LogoCC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International