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Xanthene[n]arenes: Exceptionally Large, Bowl-shaped Macrocyclic Building Blocks Suitable for Self-Assembly

preprint
submitted on 24.03.2021, 14:36 and posted on 25.03.2021, 08:31 by Jonathan Pfeuffer-Rooschüz, Alessandro Prescimone, Konrad Tiefenbacher
A new class of macrocycles denoted as “xanthene[n]arenes” was synthesized. In contrast to most other macrocycles, they feature a rigid bowl-shape, required for the synthesis of cavitands and for the self-assembly to molecular capsules via non-covalent interactions. The derivatization potential of the novel macrocycles was demonstrated on the xanthene[3]arene scaffold. Beside a deep cavitand, a modified macrocycle was synthesized that self-assembles into a hydrogen-bonded tetrameric capsule. Both supramolecular systems display host-guest binding properties, demonstrating the potential of xanthene[n]arenes as a new set of macrocyclic building blocks.

Funding

Swiss National Science Foundation 200021_178714

History

Email Address of Submitting Author

konrad.tiefenbacher@unibas.ch

Institution

University of Basel

Country

Switzerland

ORCID For Submitting Author

0000-0002-3351-6121

Declaration of Conflict of Interest

No conflict

Exports

ChemRxiv

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