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The sharp structural switch of covalent cages mediated by subtle variation of directing groups

It is considered a more formidable task to precisely control the self-assembled products containing purely covalent components, due to a lack of intrinsic templates such as transition metals to suppress entropy loss during self-assembly. Here, we attempt to tackle this challenge by using directing g...

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Autores principales: Chen, Qiong, Li, Zhaoyong, Lei, Ye, Chen, Yixin, Tang, Hua, Wu, Guangcheng, Sun, Bin, Wei, Yuxi, Jiao, Tianyu, Zhang, Songna, Huang, Feihe, Wang, Linjun, Li, Hao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10397198/
https://www.ncbi.nlm.nih.gov/pubmed/37532710
http://dx.doi.org/10.1038/s41467-023-40255-4
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author Chen, Qiong
Li, Zhaoyong
Lei, Ye
Chen, Yixin
Tang, Hua
Wu, Guangcheng
Sun, Bin
Wei, Yuxi
Jiao, Tianyu
Zhang, Songna
Huang, Feihe
Wang, Linjun
Li, Hao
author_facet Chen, Qiong
Li, Zhaoyong
Lei, Ye
Chen, Yixin
Tang, Hua
Wu, Guangcheng
Sun, Bin
Wei, Yuxi
Jiao, Tianyu
Zhang, Songna
Huang, Feihe
Wang, Linjun
Li, Hao
author_sort Chen, Qiong
collection PubMed
description It is considered a more formidable task to precisely control the self-assembled products containing purely covalent components, due to a lack of intrinsic templates such as transition metals to suppress entropy loss during self-assembly. Here, we attempt to tackle this challenge by using directing groups. That is, the self-assembly products of condensing a 1:2 mixture of a tetraformyl and a biamine can be precisely controlled by slightly changing the substituent groups in the aldehyde precursor. This is because different directing groups provide hydrogen bonds with different modes to the adjacent imine units, so that the building blocks are endowed with totally different conformations. Each conformation favors the formation of a specific product that is thus produced selectively, including chiral and achiral cages. These results of using a specific directing group to favor a target product pave the way for accomplishing atom economy in synthesizing purely covalent molecules without relying on toxic transition metal templates.
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spelling pubmed-103971982023-08-04 The sharp structural switch of covalent cages mediated by subtle variation of directing groups Chen, Qiong Li, Zhaoyong Lei, Ye Chen, Yixin Tang, Hua Wu, Guangcheng Sun, Bin Wei, Yuxi Jiao, Tianyu Zhang, Songna Huang, Feihe Wang, Linjun Li, Hao Nat Commun Article It is considered a more formidable task to precisely control the self-assembled products containing purely covalent components, due to a lack of intrinsic templates such as transition metals to suppress entropy loss during self-assembly. Here, we attempt to tackle this challenge by using directing groups. That is, the self-assembly products of condensing a 1:2 mixture of a tetraformyl and a biamine can be precisely controlled by slightly changing the substituent groups in the aldehyde precursor. This is because different directing groups provide hydrogen bonds with different modes to the adjacent imine units, so that the building blocks are endowed with totally different conformations. Each conformation favors the formation of a specific product that is thus produced selectively, including chiral and achiral cages. These results of using a specific directing group to favor a target product pave the way for accomplishing atom economy in synthesizing purely covalent molecules without relying on toxic transition metal templates. Nature Publishing Group UK 2023-08-02 /pmc/articles/PMC10397198/ /pubmed/37532710 http://dx.doi.org/10.1038/s41467-023-40255-4 Text en © The Author(s) 2023 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons licence, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons licence, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons licence and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this licence, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Chen, Qiong
Li, Zhaoyong
Lei, Ye
Chen, Yixin
Tang, Hua
Wu, Guangcheng
Sun, Bin
Wei, Yuxi
Jiao, Tianyu
Zhang, Songna
Huang, Feihe
Wang, Linjun
Li, Hao
The sharp structural switch of covalent cages mediated by subtle variation of directing groups
title The sharp structural switch of covalent cages mediated by subtle variation of directing groups
title_full The sharp structural switch of covalent cages mediated by subtle variation of directing groups
title_fullStr The sharp structural switch of covalent cages mediated by subtle variation of directing groups
title_full_unstemmed The sharp structural switch of covalent cages mediated by subtle variation of directing groups
title_short The sharp structural switch of covalent cages mediated by subtle variation of directing groups
title_sort sharp structural switch of covalent cages mediated by subtle variation of directing groups
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10397198/
https://www.ncbi.nlm.nih.gov/pubmed/37532710
http://dx.doi.org/10.1038/s41467-023-40255-4
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