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Theoretical insights into aggregation-induced helicity modulation of a perylene bisimide derivative
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Theoretical Chemistry and Biology.ORCID iD: 0000-0001-6508-8355
2018 (English)In: Journal of Molecular Modeling, ISSN 1610-2940, E-ISSN 0948-5023, Vol. 24, no 3, article id 51Article in journal (Refereed) Published
Abstract [en]

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 pi-pi 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 pi-pi 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.

Place, publisher, year, edition, pages
Springer, 2018. Vol. 24, no 3, article id 51
Keywords [en]
Supramolecular helicity, Aggregation-induced chirality, Self-assembly, Circular dichroism, Exciton model
National Category
Biochemistry and Molecular Biology
Identifiers
URN: urn:nbn:se:kth:diva-224685DOI: 10.1007/s00894-018-3591-1ISI: 000426730900007PubMedID: 29435668Scopus ID: 2-s2.0-85042265877OAI: oai:DiVA.org:kth-224685DiVA, id: diva2:1193066
Note

QC 20180326

Available from: 2018-03-26 Created: 2018-03-26 Last updated: 2018-03-26Bibliographically approved

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Li, Xin

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