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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...
3.2K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

3.1K
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...
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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

4.5K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
4.5K
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds01:14

π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds

1.4K
In aromatic compounds, such as benzene, the circulation of (4n + 2) π-electrons sets up a diamagnetic or diatropic ring current around the perimeter of the molecule. This current induces a magnetic field that opposes the external field inside the ring and reinforces it on the outside. The protons in benzene are deshielded and exhibit high chemical shifts in the range 6.5–8.5 ppm. The shielding effect at the center of the ring is evident in complex aromatic molecules, such as...
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Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

10.3K
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).
10.3K
π Molecular Orbitals of 1,3-Butadiene01:24

π Molecular Orbitals of 1,3-Butadiene

10.2K
Conjugated dienes have lower heats of hydrogenation than cumulated and isolated dienes, making them more stable. The enhanced stabilization of conjugated systems can be understood from their π molecular orbitals.
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...
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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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Nonbenzenoid High-Spin Polycyclic Hydrocarbons Generated by Atom Manipulation.

Shantanu Mishra1, Shadi Fatayer1, Saleta Fernández2

  • 1IBM Research-Zurich, 8803 Rüschlikon, Switzerland.

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|February 8, 2022
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Summary
This summary is machine-generated.

Researchers synthesized a nonbenzenoid triradical molecule using scanning tunneling microscopy to break C-H bonds in truxene. This opens pathways for creating novel high-spin polycyclic frameworks for advanced magnetic applications.

Keywords:
atomic force microscopydensity functional theorynonbenzenoid hydrocarbonson-surface synthesisopen-shell moleculesscanning tunneling microscopy

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Area of Science:

  • Organic Chemistry
  • Surface Science
  • Materials Science

Background:

  • Polycyclic aromatic hydrocarbons (PAHs) are building blocks for advanced materials.
  • High-spin organic molecules are crucial for molecular magnetism.
  • On-surface synthesis offers precise control over molecular structures and properties.

Purpose of the Study:

  • To achieve the on-surface synthesis of a nonbenzenoid triradical.
  • To characterize the synthesized molecule and its intermediates at the single-molecule level.
  • To explore the potential of this synthesis strategy for creating novel high-spin polycyclic frameworks.

Main Methods:

  • On-surface dehydrogenation of truxene using voltage pulses from a scanning tunneling microscope/atomic force microscope.
  • Single-molecule characterization using atomic force microscopy, scanning tunneling microscopy, and scanning tunneling spectroscopy.
  • Density functional theory (DFT) calculations for theoretical predictions and analysis.

Main Results:

  • Successful synthesis of truxene-5,10,15-triyl (1), a nonbenzenoid triradical, via C-H bond cleavage.
  • Characterization of the quartet ground state of molecule 1 on a NaCl/Cu(111) surface.
  • Imaging of frontier orbital densities, confirming spin-split singly occupied molecular orbitals.
  • Isolation and characterization of radical and indeno[1,2-a]fluorene intermediates with predicted doublet and triplet ground states.

Conclusions:

  • The developed on-surface synthesis method enables the creation of nonbenzenoid high-spin molecules.
  • The synthesized triradical retains its predicted quartet ground state on an insulating surface.
  • This work provides a foundation for designing and synthesizing novel organic magnetic materials.
  • Findings contribute to the understanding of magnetism beyond Lieb's theorem in polycyclic frameworks.