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Related Concept Videos

Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

16.0K
This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
16.0K
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

4.5K
Introduction
A comparison of the enthalpies of hydrogenation of dienes reveals that conjugated dienes release less heat on hydrogenation, rendering them more stable than their nonconjugated analogs.
4.5K
Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

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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.
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Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

19.7K
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...
19.7K
Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

3.7K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
3.7K
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

3.5K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
3.5K

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Dibenzohexacene: Stabilization Through Additional Clar Sextets.

Elias C Rüdiger1, Matthias Müller1, Silke Koser1

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

Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 5, 2017
PubMed
Summary
This summary is machine-generated.

Triphenylene units stabilize hexacenes, creating dibenzohexacenes. These compounds exhibit hexacene-like properties and show promising charge carrier mobility for organic electronics.

Keywords:
UV/Vis spectroscopyacenesclar sextetfluorescencehexacene

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Area of Science:

  • Organic chemistry
  • Materials science
  • Physical chemistry

Background:

  • Linear acenes are prone to instability.
  • Stabilizing acene structures is crucial for developing organic electronic materials.

Purpose of the Study:

  • To synthesize and characterize novel dibenzohexacene compounds.
  • To investigate the electronic properties and stability of these dibenzohexacenes.

Main Methods:

  • Yamamoto coupling of dibromobenzene with dibromo-TIPS-pentacene.
  • Stille coupling with dimethyldibenzostannole.
  • UV/Vis spectroscopy and quantum chemical calculations.
  • Charge carrier mobility measurements.

Main Results:

  • Successful synthesis of dibenzohexacenes through cross-coupling reactions.
  • UV/Vis spectroscopy and calculations confirmed hexacene-type electronic character.
  • Redshifted absorption characteristics indicate extended π-conjugation.
  • Dibenzohexacene 1a demonstrated a charge carrier mobility of up to 0.2 cm²/Vs.

Conclusions:

  • Triphenylene units effectively stabilize hexacene cores.
  • Dibenzohexacenes retain key hexacene electronic properties.
  • These findings offer potential for new organic semiconductor materials.