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

ABSTRACT: 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.

SUBMITTER: Pfeuffer-Rooschuz J

PROVIDER: S-EPMC8611668 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature

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Xanthene[<i>n</i>]arenes: Exceptionally Large, Bowl-Shaped Macrocyclic Building Blocks Suitable for Self-Assembly.

Pfeuffer-Rooschüz Jonathan J Schmid Lucius L Prescimone Alessandro A Tiefenbacher Konrad K

JACS Au 20211019 11

A new class of macrocycles denoted as "xanthene[<i>n</i>]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 ...[more]

PMID: 34841407

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