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Conformations of Cyclohexane02:11

Conformations of Cyclohexane

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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...
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Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

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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...
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Crystal Field Theory - Tetrahedral and Square Planar Complexes02:46

Crystal Field Theory - Tetrahedral and Square Planar Complexes

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Tetrahedral Complexes
Crystal field theory (CFT) is applicable to molecules in geometries other than octahedral. In octahedral complexes, the lobes of the dx2−y2 and dz2 orbitals point directly at the ligands. For tetrahedral complexes, the d orbitals remain in place, but with only four ligands located between the axes. None of the orbitals points directly at the tetrahedral ligands. However, the dx2−y2 and dz2 orbitals (along the Cartesian axes) overlap with the ligands less than the dxy,...
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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...
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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

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Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
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A Stable Hexaazaoctacene Cruciform σ-Dimer.

Steffen Maier1, Fabian Jester1, Marvin T Hoffmann2,3

  • 1Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Advanced Science (Weinheim, Baden-Wurttemberg, Germany)
|July 27, 2022
PubMed
Summary

Researchers synthesized a stable bi(hexaazaoctacenyl) molecule using Buchwald-Hartwig coupling and oxidation. This new organic semiconductor demonstrates remarkable persistence in both solution and crystalline states.

Keywords:
acenesazaoctacenebiacenylheteroaceneoctacenestabilization

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Azaacenes are nitrogen-containing polycyclic aromatic hydrocarbons with unique electronic properties.
  • Developing stable, processable azaacene derivatives is crucial for organic electronics.
  • Previous research faced challenges with azaacene stability and solubility.

Purpose of the Study:

  • To synthesize a novel, stable dihydrohexaazaoctacene derivative.
  • To investigate the stability and properties of the resulting bi(hexaazaoctacenyl) compound.
  • To explore the potential of protected azaacenes in materials science.

Main Methods:

  • Buchwald-Hartwig cross-coupling reaction between a TIPS-ethynylated dibromo-N,N'-dihydrotetraazapentacene and a TIPS-ethynyl-diaminonaphthalene derivative.
  • Oxidation of the synthesized dihydrohexaazaoctacene using manganese dioxide (MnO2).
  • Characterization of the final bi(hexaazaoctacenyl) product, including stability studies in solution and crystalline states.

Main Results:

  • Successful synthesis of a dihydrohexaazaoctacene via Buchwald-Hartwig coupling.
  • Formation of a 7,7'-bi(hexaazaoctacenyl) through oxidation.
  • The bi(hexaazaoctacenyl) exhibits exceptional stability, with a half-life of over 5 days in dilute solution and persistence for over 10 months in the crystalline state.
  • The triisopropylsilyl (TIPS)-ethynyl groups effectively protect the azaoctacene subunits.

Conclusions:

  • The developed synthetic strategy provides access to highly stable azaacene derivatives.
  • The bi(hexaazaoctacenyl) represents a promising new material for applications requiring robust organic semiconductors.
  • Protection of the azaoctacene core with bulky substituents significantly enhances molecular stability.