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

Angewandte Chemie
Markus HechtFrank Würthner

Abstract

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-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.

References

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Citations

Oct 24, 2020·Chemical Communications : Chem Comm·Matthias LehmannFrank Würthner
Dec 9, 2020·Accounts of Chemical Research·Markus Hecht, Frank Würthner
Mar 24, 2021·Journal of the American Chemical Society·Michihisa UedaYoshimitsu Itoh
Apr 17, 2021·Angewandte Chemie·Xiaoning LiuShaodong Zhang

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Methods Mentioned

BETA
scanning
atomic force microscopy
AFM
optical microscopy
X‐ray

Software Mentioned

COMPASS
CLEARER
Accelrys Materials Studio

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