Dispersion-Driven Formation of Chiral Twisted PAH Double Helices [Data]

DOI

Molecular double helices are ubiquitous in nature and have also been generated artificially. These are usually based on helical ribbons. Here, a new type of double helices based on twisted ribbons is introduced. The monomeric strands are polycyclic aromatic hydrocarbons of various lengths with up to 25 linearly annulated six-membered rings. Single-crystal X-ray structure analysis of all revealed that the major driving force are multiple dispersion interactions of alkyl substituents. The thermodynamic stability and formation of the twisted double helices were studied by NMR as well as the kinetics of their inversions by circular dichroism spectroscopy. In combination with theoretical calculations, the mechanism of isomerization is suggested to depend on the rate of monomerization of double helical strands rather than the double helices racemize themselves as intact pairs. The new type of twisted nanoribbons in combination with their aromatic nature opens up new possibilities to design chiral materials.

Identifier
DOI https://doi.org/10.11588/data/BRM2DI
Related Identifier https://doi.org/10.1016/j.chempr.2023.12.023
Metadata Access https://heidata.uni-heidelberg.de/oai?verb=GetRecord&metadataPrefix=oai_datacite&identifier=doi:10.11588/data/BRM2DI
Provenance
Creator Yang, Xuan; Brückner, Margit; Rominger, Frank; Kirschbaum, Tobias; Mastalerz, Michael ORCID logo
Publisher heiDATA
Contributor Mastalerz, Michael
Publication Year 2024
Funding Reference Deutsche Forschungsgemeinschaft SFB 1249 (TP-A04)
Rights CC BY 4.0; info:eu-repo/semantics/openAccess; http://creativecommons.org/licenses/by/4.0
OpenAccess true
Contact Mastalerz, Michael (Institute of Organic Chemistry, Heidelberg University)
Representation
Resource Type Dataset
Format application/zip
Size 373919985; 485909048; 363080836; 210511553; 249705458; 77705108; 80453791; 71619089; 166942262; 80364553; 175013730; 76705717; 77269560; 78985105; 84879874; 83911668; 190691717; 1671753
Version 1.0
Discipline Chemistry; Natural Sciences