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

A new class of macrocycles denoted as “xanthene­[n]­arenes” was synthesized. In contrast to most other macrocycles, they feature a conformationally restricted bowl shape due to the attached alkyl groups at the linking methylene units. This facilitates the synthesis of cavitands and the self-assembly...

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Bibliographic Details
Published in:JACS Au 2021-11, Vol.1 (11), p.1885-1891
Main Authors: Pfeuffer-Rooschüz, Jonathan, Schmid, Lucius, Prescimone, Alessandro, Tiefenbacher, Konrad
Format: Article
Language:English
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Letter
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Summary:A new class of macrocycles denoted as “xanthene­[n]­arenes” was synthesized. In contrast to most other macrocycles, they feature a conformationally restricted bowl shape due to the attached alkyl groups at the linking methylene units. This facilitates the synthesis of cavitands and the self-assembly to molecular capsules via noncovalent interactions. The derivatization potential of the novel macrocycles was demonstrated on the xanthene[3]­arene scaffold. Besides a deep cavitand and an oxygen-embedded zigzag hydrocarbon belt[12]­arene, a modified macrocycle was synthesized that self-assembles into a hydrogen-bonded tetrameric capsule, demonstrating the potential of xanthene­[n]­arenes as a new set of macrocyclic building blocks.
ISSN:2691-3704
2691-3704
DOI:10.1021/jacsau.1c00343