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Pericyclic Reactions: Introduction

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Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Published on: February 6, 2020

Dissipative Assembly of Macrocycles Comprising Multiple Transient Bonds.

Mohammad Mosharraf Hossain¹, Joshua L Atkinson¹, C Scott Hartley¹

¹Department of Chemistry & Biochemistry, Miami University, Oxford, OH, 45056, USA.

Angewandte Chemie (International Ed. in English)

|May 9, 2020

Summary

Chemical fuels can now assemble complex macrocycles with multiple transient bonds from simple components. This breakthrough enables the creation of sophisticated, adaptive chemical systems beyond equilibrium constraints.

Keywords:

aggregation anhydrides dissipative assembly macrocycles self-assembly

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Area of Science:

Chemistry
Materials Science
Chemical Engineering

Background:

Dissipative assembly offers potential for adaptive chemical systems.
Equilibrium-based molecular assembly creates complex structures, unlike simple out-of-equilibrium systems.

Purpose of the Study:

To demonstrate chemical fuels assembling bifunctional components into macrocycles with multiple transient bonds.
To explore the mechanisms behind fuel-driven macrocycle formation and stability.

Main Methods:

Treatment of dicarboxylic acids with a carbodiimide to form aqueous dianhydride macrocycles.
Analysis of fuel-dependent and fuel-independent assembly mechanisms.
Investigation of macrocycle decomposition and dynamic bond exchange.

Main Results:

Efficient assembly of macrocycles containing multiple transient anhydride bonds was achieved.
Both fuel-dependent and fuel-independent mechanisms contribute to macrocycle formation.
Macrocycles exhibit slower decomposition and are favored by dynamic exchange of anhydride bonds.

Conclusions:

Chemical fuels can drive the formation of structurally complex, out-of-equilibrium species.
This work expands possibilities for creating sophisticated adaptive chemical systems.
The developed method allows for the generation of macrocycles with multiple transient bonds.