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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.3K
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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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
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

12.0K
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.
12.0K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.5K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.5K
Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

2.7K
The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
2.7K
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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Surface-Confined Macrocyclization via Dynamic Covalent Chemistry.

Chaoying Fu1,2,3, Jiří Mikšátko4, Lea Assies4

  • 1Center Lab of Longhua Branch and Department of Infectious disease, Shenzhen People's Hospital, second Clinical Medical College of Jinan University, Shenzhen 518120, Guangdong Province, China.

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|February 19, 2020
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Summary
This summary is machine-generated.

Researchers achieved selective synthesis of monodisperse macrocycles using surface-confined dynamic covalent chemistry. Tailoring alkyl substituents controlled product formation, enabling precise molecular nanostructure construction.

Keywords:
density functional theorydynamic covalent chemistrymacrocyclemolecular dynamics simulationon-surface synthesisscanning tunneling microscopy

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Nanotechnology

Background:

  • Surface-confined synthesis offers a route to complex molecular nanostructures like macrocycles.
  • On-surface macrocyclization faces challenges in selectivity for monodisperse and multicomponent structures.

Purpose of the Study:

  • To report the on-surface formation of [6 + 6] Schiff-base macrocycles via dynamic covalent chemistry.
  • To investigate methods for selective synthesis of monodisperse macrocycles on surfaces.
  • To understand the factors influencing macrocycle formation over oligomers or polymers.

Main Methods:

  • Utilized dynamic covalent chemistry for on-surface macrocyclization.
  • Employed in situ scanning tunneling microscopy (STM) for real-time imaging.
  • Integrated density functional theory (DFT) and molecular dynamics (MD) simulations for mechanistic insights.

Main Results:

  • Achieved formation of two-dimensional crystalline domains of [6 + 6] Schiff-base macrocycles.
  • Demonstrated control over product formation (oligomers, macrocycles, polymers) by adjusting alkyl substituent length.
  • Identified synergistic effects of surface confinement and solvent in promoting macrocyclization.

Conclusions:

  • On-surface dynamic covalent chemistry enables the selective synthesis of well-defined macrocycles.
  • Alkyl chain length is a critical parameter for controlling supramolecular assembly on surfaces.
  • Surface confinement and solvent play crucial roles in directing molecular self-assembly and macrocyclization.