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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

2.9K
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...
2.9K
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

12.2K
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....
12.2K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

2.9K
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...
2.9K
Stability of Substituted Cyclohexanes02:30

Stability of Substituted Cyclohexanes

12.8K
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...
12.8K
Conformations of Cycloalkanes02:29

Conformations of Cycloalkanes

12.0K
Adolf von Baeyer attempted to explain the instabilities of small and large cycloalkane rings using the concept of angle strain — the strain caused by the deviation of bond angles from the ideal 109.5° tetrahedral value for sp3  hybridized carbons. However, while cyclopropane and cyclobutane are strained, as expected from their highly compressed bond angles, cyclopentane is more strained than predicted, and cyclohexane is virtually strain-free. Hence, Baeyer’s theory that...
12.0K
Chair Conformation of Cyclohexane02:02

Chair Conformation of Cyclohexane

14.9K
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...
14.9K

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Substituted Cyclopentannulated Tetraazapentacenes.

Steffen Maier1, Robin Heckershoff1, Nikolai Hippchen1

  • 1Organisch-Chemisches Institut (OCI), Heidelberg University, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 19, 2022
PubMed
Summary

Researchers synthesized novel brominated pentannulated dihydrotetraazapentacenes. These compounds show potential as n-type semiconductors, confirmed by organic field-effect transistor characterization.

Keywords:
cyclizationdihydroazaacenespostfunctionalizationsemiconductorssolid-state packing

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Semiconductor Physics

Background:

  • Dihydrotetraazapentacenes are a class of organic molecules with potential electronic applications.
  • Developing new synthetic routes and functionalization methods is crucial for exploring their properties.

Purpose of the Study:

  • To synthesize novel brominated pentannulated dihydrotetraazapentacenes.
  • To investigate their potential as n-type semiconductors.
  • To explore post-functionalization strategies.

Main Methods:

  • Gold- or palladium-catalyzed 5-endo-dig cyclization of TIPS-ethynylated dihydrotetraazaacenes.
  • Post-functionalization via Sonogashira alkynylation and Rosenmund-von Braun cyanation.
  • Computational calculations and characterization in organic field-effect transistors.

Main Results:

  • Successful synthesis of brominated pentannulated dihydrotetraazapentacenes.
  • Demonstration of post-functionalization capabilities.
  • Computational predictions of n-type semiconducting behavior.
  • Experimental verification of n-type semiconducting properties in two derivatives.

Conclusions:

  • The developed synthetic strategy enables access to novel functionalized dihydrotetraazapentacenes.
  • These compounds exhibit promising n-type semiconductor characteristics.
  • The findings open avenues for further development of organic electronic materials.