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Theoretical insights into aggregation-induced helicity modulation of a perylene bisimide derivative

  • Lijun Liang
  • Xin Li
Original Paper

Abstract

Formation of helical chiroptical self-assemblies via noncovalent interaction is a widely observed phenomenon in nature, the mechanism of which remains insufficiently understood. Employing an amphiphilic perylene–sugar dyad molecule (PBI-HAG) as an example, we report that the modulatable supramolecular helicity may emerge from an aggregating process that is dominated by competition between two types of noncovalent interaction: hydrogen bonding and π–π stacking. The interplay between these two driving forces, which is greatly affected by the solvent environment, determines the morphology the supramolecular assembly of PBI-HAGs. In particular, a non-layered supramolecular structure was formed in octane owing to stabilization effects of intermolecular hydrogen bonds, whereas a layered supramolecular structure was formed in water because of energetically favorable π–π stacking of aromatic rings. The formation of distinct supramolecular architectures in different solvents was reinforced by simulated circular dichroism spectra, which show opposite signals consistent with experimental observations. The results of this study could help us understand aggregation-induced supramolecular chirality of noncovalent self-assemblies.

Graphical abstract

Left Typical structures of amphiphilic perylene–sugar dyad (PBI-HAG) aggregates in different octane and water. Right Simulated CD and UV-Vis spectra of core PBIs aggregates in octane and water

Keywords

Supramolecular helicity Aggregation-induced chirality Self-assembly Circular dichroism Exciton model 

Notes

Acknowledgments

We acknowledge financial support by the National Natural Science Foundation of China (Grant Nos. 21503186, 21674032).

Author contributions

X.L. designed the study. X.L. and L.L. carried out the calculations, analyzed the data and wrote the paper.

Compliance with ethical standards

Competing financial interests

The authors declare no competing financial interest.

Supplementary material

894_2018_3591_MOESM1_ESM.doc (524 kb)
ESM 1 (DOC 524 kb)

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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.College of Life Information Science and Instrument EngineeringHangzhou Dianzi UniversityHangzhouPeople’s Republic of China
  2. 2.Division of Theoretical Chemistry & Biology, School of BiotechnologyKTH Royal Institute of TechnologyStockholmSweden

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