ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
2 files

Dimeric and Trimeric Catenation of Giant Chiral [8+12] Imine Cubes Driven by Weak Supramolecular Interactions

preprint
submitted on 09.04.2021, 13:25 and posted on 12.04.2021, 12:37 by Bahiru Punja Benke, Tobias Kirschbaum, Jürgen Graf, Michael Mastalerz
Mechanically interlocked structures, such as catenanes or rotaxanes are fascinating synthetic targets and are the basis of molecular switches and machines. Today, the vast majority of catenated structures are built upon macrocycles and only a very few examples of three?dimensional shape-persistent organic cages forming such structures are reported. However, the catenation in all these cases was based on a thermodynamically favoured π-π stacking under certain reaction conditions. Here, we present our findings that catenane formation can be driven by even less directional dispersion (Keesom) interactions of methoxy-groups during the synthesis of chiral [8+12] imine cubes, giving dimeric and also for the first time trimeric catenated organic cages. To further elucidate the underlying driving forces, twelve differently 1,4-substituted benzene dialdehydes have been reacted with a chiral triamino tribenzotriquinacene under various conditions to study whether monomeric cages or catenated cage dimers are the preferred products.

Funding

ERC consolidators grant CaTs n DOCs (725765)

History

Email Address of Submitting Author

michael.mastalerz@oci.uni-heidelberg.de

Institution

Ruprecht-Karls-Universität Heidelberg

Country

Germany

ORCID For Submitting Author

0000-0003-3231-4816

Declaration of Conflict of Interest

no conflict of interest

Version Notes

1st version

Exports

ChemRxiv

Exports