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Related Concept Videos

Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

10.8K
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....
10.8K
Nomenclature of Alkynes02:39

Nomenclature of Alkynes

18.3K
Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
18.3K
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

5.5K
Introduction
Conjugated dienes are compounds characterized by the presence of alternating double and single bonds. In a conjugated system like 1,3-butadiene, the unhybridized 2p orbital on each carbon overlaps continuously, allowing the π electrons to be delocalized across the entire molecule. In contrast, this type of overlap does not occur in cumulated and isolated dienes, such as 2,3-pentadiene and 1,4-pentadiene, respectively. Instead, the π electrons remain localized between the...
5.5K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

8.0K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
8.0K
Stability of Conjugated Dienes01:28

Stability of Conjugated Dienes

3.4K
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.
3.4K
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

3.5K
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

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Related Experiment Video

Updated: May 2, 2026

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
06:55

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level

Published on: September 26, 2016

8.5K

Hexacene Diimides.

Xiaoping Cui1,2, Chengyi Xiao3, Thorsten Winands4

  • 1Key Laboratory of Organic Optoelectronics and Molecular Engineering, Department of Chemistry , Tsinghua University , Beijing 100084 , China.

Journal of the American Chemical Society
|August 23, 2018
PubMed
Summary
This summary is machine-generated.

Researchers synthesized large hexacene diimides (HDI) with improved solubility and stability. These novel organic semiconductors show significantly smaller band gaps and excellent performance in organic field-effect transistors (OFETs).

Related Experiment Videos

Last Updated: May 2, 2026

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
06:55

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level

Published on: September 26, 2016

8.5K

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Semiconductor Physics

Background:

  • Acene imides offer potential for smaller band gaps compared to acenes, with maintained solubility and stability.
  • Synthesizing large acene imides remains a significant challenge in materials development.

Purpose of the Study:

  • To develop a facile synthesis for large acene imides, specifically hexacene diimides (HDIs).
  • To investigate the electronic and physical properties of the synthesized HDIs.
  • To evaluate the performance of HDIs in organic field-effect transistors (OFETs).

Main Methods:

  • A one-pot synthesis strategy involving double aromatic annulation.
  • Utilized zirconabenzocyclopentene and tetrabrominated naphthalene diimides as precursors.
  • Fabrication and characterization of organic field-effect transistors (OFETs) using HDI microribbons.

Main Results:

  • Successfully synthesized hexacene diimides (HDIs) via a novel one-pot method.
  • HDIs with branched alkyl chains demonstrated excellent solubility and stability.
  • Achieved significantly smaller band gaps compared to hexacene.
  • OFETs based on HDI microribbons exhibited ambipolar transport with high electron mobility (2.17 cm² V⁻¹ s⁻¹) and hole mobility (0.30 cm² V⁻¹ s⁻¹).

Conclusions:

  • The developed one-pot synthesis provides an effective route to large acene imides.
  • Synthesized HDIs possess desirable electronic properties for organic electronics applications.
  • The high charge carrier mobilities indicate the potential of HDIs in advanced OFET devices.