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

[Image: see text] 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 t...

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Autores principales: Pfeuffer-Rooschüz, Jonathan, Schmid, Lucius, Prescimone, Alessandro, Tiefenbacher, Konrad
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8611668/
https://www.ncbi.nlm.nih.gov/pubmed/34841407
http://dx.doi.org/10.1021/jacsau.1c00343
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author Pfeuffer-Rooschüz, Jonathan
Schmid, Lucius
Prescimone, Alessandro
Tiefenbacher, Konrad
author_facet Pfeuffer-Rooschüz, Jonathan
Schmid, Lucius
Prescimone, Alessandro
Tiefenbacher, Konrad
author_sort Pfeuffer-Rooschüz, Jonathan
collection PubMed
description [Image: see text] 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.
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spelling pubmed-86116682021-11-26 Xanthene[n]arenes: Exceptionally Large, Bowl-Shaped Macrocyclic Building Blocks Suitable for Self-Assembly Pfeuffer-Rooschüz, Jonathan Schmid, Lucius Prescimone, Alessandro Tiefenbacher, Konrad JACS Au [Image: see text] 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. American Chemical Society 2021-10-19 /pmc/articles/PMC8611668/ /pubmed/34841407 http://dx.doi.org/10.1021/jacsau.1c00343 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Pfeuffer-Rooschüz, Jonathan
Schmid, Lucius
Prescimone, Alessandro
Tiefenbacher, Konrad
Xanthene[n]arenes: Exceptionally Large, Bowl-Shaped Macrocyclic Building Blocks Suitable for Self-Assembly
title Xanthene[n]arenes: Exceptionally Large, Bowl-Shaped Macrocyclic Building Blocks Suitable for Self-Assembly
title_full Xanthene[n]arenes: Exceptionally Large, Bowl-Shaped Macrocyclic Building Blocks Suitable for Self-Assembly
title_fullStr Xanthene[n]arenes: Exceptionally Large, Bowl-Shaped Macrocyclic Building Blocks Suitable for Self-Assembly
title_full_unstemmed Xanthene[n]arenes: Exceptionally Large, Bowl-Shaped Macrocyclic Building Blocks Suitable for Self-Assembly
title_short Xanthene[n]arenes: Exceptionally Large, Bowl-Shaped Macrocyclic Building Blocks Suitable for Self-Assembly
title_sort xanthene[n]arenes: exceptionally large, bowl-shaped macrocyclic building blocks suitable for self-assembly
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8611668/
https://www.ncbi.nlm.nih.gov/pubmed/34841407
http://dx.doi.org/10.1021/jacsau.1c00343
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