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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.5K
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.
3.5K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.5K
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.
2.5K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

9.9K
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.
9.9K
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

8.2K
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...
8.2K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.0K
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.
2.0K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.3K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.3K

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Updated: May 29, 2025

Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry
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Redirecting On-surface Cycloaddition Reactions in a Self-assembled Ordered Molecular Array on Graphite.

Yu Li Huang1, Ke Yang2, Jing Yang3

  • 1Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, Fuzhou, 350207, China.

Angewandte Chemie (International Ed. in English)
|February 5, 2025
PubMed
Summary
This summary is machine-generated.

Synthesizing carbon nanostructures on inert graphite surfaces is challenging due to desorption. This study reveals a novel cycloaddition mechanism on graphite, enabling large supramolecular islands via mild annealing.

Keywords:
Fe catalystcycloaddition reactionsgraphiteon-surface synthesisself-assembled supramolecular arrays

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Preparation of Carbon Nanosheets at Room Temperature
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Preparation of Carbon Nanosheets at Room Temperature
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Area of Science:

  • Surface Science
  • Materials Chemistry
  • Nanotechnology

Background:

  • Atomically precise carbon nanostructure synthesis is advanced on metal surfaces.
  • Synthesis on inert surfaces is difficult due to thermal desorption.
  • Weak substrate interactions hinder C-C coupling on non-metal surfaces.

Purpose of the Study:

  • To investigate on-surface synthesis of carbon nanostructures on graphite.
  • To overcome the desorption problem on inert surfaces.
  • To understand the mechanism of cycloaddition reactions on graphite.

Main Methods:

  • Utilizing scanning tunneling microscopy (STM) for in-situ observation.
  • Employing mild annealing (~210°C) to trigger reactions.
  • Conducting first-principles calculations to analyze reaction pathways.

Main Results:

  • An extraordinary [2+2]+[2+2] cycloaddition reaction was achieved on graphite.
  • Large supramolecular islands of cycloaddition products and polymers formed (>30%).
  • A novel driving mechanism involving intermolecular coupling, steric hindrance, and interfacial interactions was identified.

Conclusions:

  • This study presents a new paradigm for on-surface synthesis on non-metal substrates.
  • Mild annealing and surface interactions enable controlled synthesis on graphite.
  • The findings pave the way for designing carbon nanostructures on diverse inert surfaces.