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Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

11.7K
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
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Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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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...
3.5K
Newman Projections02:06

Newman Projections

20.0K
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...
20.0K
Coordination Number and Geometry02:57

Coordination Number and Geometry

18.5K
For transition metal complexes, the coordination number determines the geometry around the central metal ion. Table 1 compares coordination numbers to molecular geometry. The most common structures of the complexes in coordination compounds are octahedral, tetrahedral, and square planar.
18.5K
Conformations of Cyclohexane02:11

Conformations of Cyclohexane

14.9K
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...
14.9K
Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

11.4K
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.
11.4K

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Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry
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A Hexabenzocoronene-Based Helical Nanographene.

Max M Martin1, Frank Hampel1, Norbert Jux1

  • 1Department of Chemistry and Pharmacy & Interdisciplinary Center for, Molecular Materials (ICMM), Organic Chemistry II, Friedrich-Alexander-University Erlangen-Nuernberg, Nikolaus-Fiebiger-Str. 10, 91058, Erlangen, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 28, 2020
PubMed
Summary
This summary is machine-generated.

Researchers developed a new method to create helical nanographene molecules. This synthesis uses a sterically hindered precursor to form a π-extended [5]helicene, a novel nanographene structure.

Keywords:
carbon allotropehelicenehexabenzocoronenenanographenepolycyclic aromatic hydrocarbons

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Nanotechnology

Background:

  • Hexabenzocoronenes are large polycyclic aromatic hydrocarbons with unique electronic properties.
  • Helical nanographenes represent a promising class of materials for advanced applications.
  • Developing efficient synthetic routes to complex nanographene architectures remains a challenge.

Purpose of the Study:

  • To develop a novel synthetic route towards hexabenzocoronene-based helical nanographene motifs.
  • To design a specific hexaphenylbenzene precursor that prevents planarization due to steric hindrance.
  • To synthesize and fully characterize a π-extended [5]helicene.

Main Methods:

  • Design and synthesis of a sterically hindered hexaphenylbenzene precursor.
  • Oxidative cyclodehydrogenation reaction to induce π-extension and helicity.
  • Comprehensive characterization, including X-ray diffraction analysis.

Main Results:

  • Successful development of a synthetic strategy for a novel helical nanographene.
  • The designed precursor effectively prevented planarization, directing the formation of a helical structure.
  • Characterization confirmed the formation of the π-extended [5]helicene motif.

Conclusions:

  • A new synthetic pathway to helical nanographenes has been established.
  • Steric control is a viable strategy for accessing complex, non-planar graphene architectures.
  • The synthesized [5]helicene represents a unique nanographene structure with potential for further research.