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

Qiong Chen, Zhaoyong Li, Ye Lei, Yixin Chen, Hua Tang, Guangcheng Wu, Bin Sun, Yuxi Wei, Tianyu Jiao, Songna Zhang (), Feihe Huang (), Linjun Wang () and Hao Li ()
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Qiong Chen: Zhejiang University
Zhaoyong Li: Zhejiang University
Ye Lei: Zhejiang University
Yixin Chen: Zhejiang University
Hua Tang: Zhejiang University
Guangcheng Wu: Zhejiang University
Bin Sun: Zhejiang University
Yuxi Wei: Zhejiang University
Tianyu Jiao: Zhejiang University
Songna Zhang: Zhejiang University
Feihe Huang: Zhejiang University
Linjun Wang: Zhejiang University
Hao Li: Zhejiang University

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract 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.

Date: 2023
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DOI: 10.1038/s41467-023-40255-4

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