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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Dynamic Covalent Self-Assembly Based on Oxime Condensation.

Libo Shen¹, Ning Cao¹, Lu Tong¹

¹Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.

Angewandte Chemie (International Ed. in English)

|October 19, 2018

Summary

This summary is machine-generated.

This study introduces a novel dynamic covalent approach using switchable oxime chemistry in water. This method enables the self-assembly of complex organic molecules, overcoming stability issues common in dynamic covalent chemistry.

Keywords:

Supramolecular chemistry catenanes dynamic covalent bonds oxime self-assembly

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Area of Science:

Supramolecular Chemistry
Organic Chemistry
Materials Science

Background:

Dynamic covalent chemistry (DCvC) relies on reversible reactions to form complex structures.
Traditional DCvC often faces challenges with the stability of self-assembled products due to their reversible nature.
Oxime bonds exhibit tunable dynamic properties based on acidity, offering a potential solution.

Purpose of the Study:

To develop a novel dynamic covalent strategy utilizing the switchable nature of oxime bonds.
To enable the self-assembly of complex organic molecules in aqueous conditions.
To enhance the stability of self-assembled products in DCvC.

Main Methods:

Employing oxime chemistry with switchable ON/OFF dynamic behavior controlled by pH.
Utilizing aqueous conditions for self-assembly processes.
Investigating the formation of catenanes and macrocycles through error-checking mechanisms.

Main Results:

Demonstrated successful self-assembly of purely organic molecules with complex topology in water.
Achieved high yields of catenane and macrocycle formation under acidic conditions (ON state).
Showcased the trapping of self-assembled products in neutral conditions (OFF state), enhancing product stability.

Conclusions:

The switchable oxime chemistry provides a robust platform for DCvC in water.
This approach effectively addresses the product stability limitations of traditional DCvC.
The developed method facilitates the construction of intricate molecular architectures with improved stability.