Related Experiment Video
Updated: Aug 29, 2025
20:28
A Toolkit to Enable Hydrocarbon Conversion in Aqueous Environments
Published on: October 2, 2012
14.2K
The taming of Clar's hydrocarbon
Leoš Valenta1, Michal Juríček1,2
1Department of Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland. michal.juricek@chem.uzh.ch.
Chemical Communications (Cambridge, England)
|September 13, 2022
Summary
Triangulene, a reactive graphene fragment, is synthesized and stabilized. Its unique electronic structure opens doors for spintronics, quantum computing, and advanced carbon materials.
Area of Science:
- Organic Chemistry
- Materials Science
- Quantum Physics
Background:
- Triangulene is the smallest non-Kekulé graphene fragment, also known as Clar's hydrocarbon.
- It possesses an open-shell electronic structure with two unpaired electrons, leading to high reactivity.
- Its triplet ground state is predicted by established quantum mechanical rules.
Purpose of the Study:
- To review the historical development of triangulene synthesis.
- To discuss methods for stabilizing reactive triangulene derivatives.
- To explore potential applications in advanced materials and quantum science.
Main Methods:
- Review of historical synthetic approaches to triangulene.
- Discussion of on-surface techniques and substituent installation for kinetic stabilization.
- Analysis of theoretical predictions regarding its electronic structure.
Main Results:
- The extreme reactivity of triangulene necessitates specific stabilization strategies.
- Persistent triangulene derivatives have been successfully synthesized.
- On-surface techniques and steric hindrance are key to stabilizing the molecule.
Conclusions:
- Triangulene's unique electronic properties make it a valuable building block for novel carbon-based materials.
- Stabilized triangulene derivatives pave the way for applications in spintronics and quantum computing.
- Continued research into triangulene synthesis and functionalization promises advancements in materials science.
More Related Videos
Related Concept Videos
02:33Physical Properties of Alkanes
11.8K
Alkanes are nonpolar molecules due to the presence of only carbon and hydrogen atoms. The electronegativity difference between carbon and hydrogen is minimal, and hence alkanes have a zero dipole moment. This leads to the presence of only dispersion forces between the molecules. The strength of dispersion forces is dependent on the surface area of the molecules on which they act. Since the surface area increases with the molecular length for straight-chain alkanes, the dispersion forces also...
11.8K
02:23Structure of Alkanes
28.7K
The formation of carbon-carbon bonds leading to the creation of the carbon chain is the basis of organic chemistry. August Kekulé and Archibald Scott Couper independently developed this idea of carbon chain formation.
Hydrocarbons are the simplest organic compounds composed of carbons and hydrogens. Based on the bond order between carbons, the hydrocarbons are further classified into alkanes, alkenes, and alkynes.
Alkanes are the simplest hydrocarbons with sp3 hybrid carbon atoms....
Hydrocarbons are the simplest organic compounds composed of carbons and hydrogens. Based on the bond order between carbons, the hydrocarbons are further classified into alkanes, alkenes, and alkynes.
Alkanes are the simplest hydrocarbons with sp3 hybrid carbon atoms....
28.7K
01:18Aromatic Hydrocarbon Anions: Structural Overview
2.9K
Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
Due to the absence of continuous...
2.9K
01:27Inductive Effects on Chemical Shift: Overview
1.3K
The protons in unsubstituted alkanes are strongly shielded with chemical shifts below 1.8 ppm. Methine, methylene, and methyl protons appear at approximately 1.7, 1.2 and 0.7 ppm, while the proton signal from methane appears at 0.23 ppm. An electronegative substituent, such as chlorine, withdraws the electron density from the protons, increasing their chemical shift. Progressive substitution of the hydrogens in methane by chlorine shifts the proton signals increasingly downfield, to 3.05 ppm in...
1.3K
01:10Hydrolysis of Chlorobenzene to Phenol: Dow Process
3.1K
Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is...
3.1K
01:18Mass Spectrometry: Long-Chain Alkane Fragmentation
1.8K
The molecular ions of linear alkanes prefer to fragment at the carbon-carbon bond away from the end of the chain since the cleavage of an inner bond creates a stable carbocation and a stable radical. Consequently, the mass signals of linear alkanes feature intense peaks in the middle of the mass-to-charge ratio plot with weaker peaks on either end. The fragmentation of each carbon-carbon bond with the release of a methyl group in each splitting leads to prominent peaks in the mass spectra...
1.8K