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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.4K
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
3.4K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

16.9K
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...
16.9K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

14.3K
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...
14.3K
Newman Projections02:06

Newman Projections

19.4K
Different notations are used to represent the three-dimensional structure of molecules on two-dimensional surfaces. One of the most commonly used representations is the dash-wedge formula. The dashed wedges, solid wedges, and the plane lines indicate the groups situated behind the plane, coming out of the plane, and in the plane, respectively.
The organic molecules rotate across the single bonds leading to numerous temporary three-dimensional structures of varying energy known as...
19.4K
Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

10.9K
In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
10.9K

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Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry
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Toward Zigzag-edged Helical Nanographene Based on [7]Helicene.

Ming-Guang Rong1, Junting Wang1, Junzhi Liu1

  • 1Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. China.

Chemistry, an Asian Journal
|March 26, 2021
PubMed
Summary

Researchers synthesized a novel zigzag-edged nanographene with a [7]helicene subunit. This unique helical diketone compound exhibits interesting photophysical and electrochemical properties, opening avenues for new nanographene synthesis.

Keywords:
Curved nanographenes.HelicenesPolycyclic aromatic hydrocarbonsZigzag edges

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Nanotechnology

Background:

  • Zigzag-edged nanographenes are of significant interest due to their unique properties.
  • Developing novel nanographene structures with specific functionalities is an ongoing challenge in materials science.

Purpose of the Study:

  • To design and synthesize a novel zigzag-edged nanographene incorporating a [7]helicene subunit.
  • To investigate the structural, photophysical, and electrochemical properties of the synthesized compound.

Main Methods:

  • Chemical synthesis of the target nanographene.
  • Single-crystal X-ray crystallography for structural elucidation.
  • UV-vis absorption spectroscopy and cyclic voltammetry for property analysis.
  • Density Functional Theory (DFT) calculations for further investigation.

Main Results:

  • Successful synthesis of a novel zigzag-edged nanographene (6) containing a [7]helicene subunit.
  • Formation of a helical diketone derivative (1) via oxidation of compound 6.
  • Unambiguous structural confirmation of the helical diketone 1 using X-ray crystallography.
  • Characterization of photophysical and electrochemical properties, including a calculated band gap of 2.94 eV via DFT.

Conclusions:

  • This study reports the first synthesis of an unprecedented [7]helicene-embedded nanographene.
  • The findings demonstrate a viable route for synthesizing complex helical nanographenes with zigzag edges.
  • The developed methods offer potential for creating new materials with tailored properties for advanced applications.