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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
4.1K
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

9.5K
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.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
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Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
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Devising Synthetic Reaction Cycles for Dissipative Nonequilibrium Self-Assembly.

Nishant Singh1, Georges J M Formon1, Serena De Piccoli1

  • 1Université de Strasbourg, 8 allée Gaspard Monge, 67000, Strasbourg, France.

Advanced Materials (Deerfield Beach, Fla.)
|February 18, 2020
PubMed
Summary

Artificial systems mimic biological self-assembly using fuel-driven reactions that form and break covalent bonds. This review explores existing chemistries, discusses their limitations, and proposes future directions for dynamic covalent self-assembly.

Keywords:
bond formationchemical fueldissipative self-assemblynon-equilibrium states

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Chemical Biology

Background:

  • Biological systems utilize fuel-driven reaction cycles to regulate the assembly and disassembly of supramolecular materials, like the cytoskeleton.
  • Fuel molecules can interact noncovalently or covalently with self-assembling building blocks, controlling the assembly process.
  • Artificial systems are being developed to replicate these dynamic behaviors observed in nature.

Purpose of the Study:

  • To review and analyze artificial systems that employ fuel-driven reaction cycles for self-assembly and disassembly via covalent bond manipulation.
  • To provide a chronological overview of different chemistries used in these systems, evaluating their respective advantages and disadvantages.
  • To outline desirable characteristics for future reaction cycles, fuels, and waste management strategies in this field.

Main Methods:

  • Literature review of chemically fueled dissipative self-assembly systems.
  • Chronological analysis of employed chemistries and their mechanistic underpinnings.
  • Discussion of pros and cons for each chemical approach.

Main Results:

  • Identification and categorization of various covalent chemistries utilized in artificial self-assembly systems.
  • Evaluation of the strengths and weaknesses of existing fuel-driven self-assembly methodologies.
  • Highlighting the need for improved fuel efficiency and waste management in artificial systems.

Conclusions:

  • Chemically fueled dissipative self-assembly offers a powerful route to dynamic artificial materials mimicking biological systems.
  • Further research is needed to optimize fuel design, reaction efficiency, and sustainability.
  • Exploration of novel chemistries, such as [suggested chemistries], holds promise for advancing the field.