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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.6K
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.
2.6K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.6K
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.
3.6K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

10.3K
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.
10.3K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

12.6K
Cyclohexane does not exist in a planar form due to the high angle and torsional strain it would experience in the planar structure. Instead, it adopts non-planar chair and boat conformations.
The chair form is the most stable and derives its name from its resemblance to the “easy chair.” In the chair conformation, two carbon atoms are arranged out-of-plane — one above and one below, minimizing the torsional strain. In the chair form, the bond angle is very close to the ideal...
12.6K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.2K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
2.2K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

14.7K
The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...
14.7K

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Updated: Jul 15, 2025

Preparation and Characterization of C60/Graphene Hybrid Nanostructures
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Extending on-surface synthesis from 2D to 3D by cycloaddition with C60.

Pengcheng Ding1, Shaoshan Wang1, Cristina Mattioli2

  • 1School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin, 150001, China.

Nature Communications
|September 28, 2023
PubMed
Summary

Researchers developed a new on-surface synthesis (OSS) method to create 3D covalently-bonded organic architectures. This approach extends 2D polymer synthesis to three dimensions using fullerene (C60) and aromatic compounds on surfaces.

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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Surface Science

Background:

  • On-surface synthesis (OSS) enables sub-molecular level investigation of intermolecular coupling and polymer formation.
  • Current OSS methods are limited to two-dimensional lateral covalent bonding within a single molecular layer.
  • Extending OSS to three-dimensional synthesis remains a significant challenge in molecular engineering.

Purpose of the Study:

  • To develop a novel on-surface synthesis strategy for creating three-dimensional covalently-bonded organic architectures.
  • To explore the perpendicular covalent coupling of fullerene (C60) with aromatic compounds on surfaces.
  • To enable precise bottom-up synthesis of complex 3D organic structures for potential device applications.

Main Methods:

  • Assembly of a C60 layer on a well-defined molecular network to facilitate molecular orbital hybridization.
  • Thermal activation to induce [4+2] cycloaddition between C60 and phenyl rings, forming perpendicular covalent bonds.
  • Characterization of the resulting adducts, including their orientation and sub-molecular features at room temperature.

Main Results:

  • Successful realization of perpendicular covalent coupling between C60 and aromatic molecules on a surface via [4+2] cycloaddition.
  • The resulting adducts exhibited frozen orientation and distinct sub-molecular features at room temperature.
  • Demonstrated subsequent lateral covalent bonding via [2+2] cycloaddition, enabling further structural extension.

Conclusions:

  • This study presents an unconventional route for the precise bottom-up synthesis of 3D covalently-bonded organic architectures on surfaces.
  • The developed method overcomes the limitations of 2D OSS, opening new possibilities for constructing complex 3D molecular structures.
  • The findings pave the way for novel 3D organic materials and devices fabricated through surface-confined synthesis.