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Related Concept Videos

Crown Ethers02:36

Crown Ethers

Crown ethers are cyclic polyethers that contain multiple oxygen atoms, usually arranged in a regular pattern. The first crown ether was synthesized by Charles Pederson while working at DuPont in 1967. For this work, Pedersen was co-awarded the 1987 Nobel Prize in Chemistry. Crown ethers are named using the formula x-crown-y, where x is the total number of atoms in the ring and y is the number of ether oxygen atoms. The term 'crown' refers to the crown-like shape that these ether molecules take.
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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 with both...
Structure of Conjugated Dienes01:16

Structure of Conjugated Dienes

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 double...
Coordination Compounds and Nomenclature02:54

Coordination Compounds and Nomenclature

In most main group element compounds, the valence electrons of the isolated atoms combine to form chemical bonds that satisfy the octet rule. For instance, the four valence electrons of carbon overlap with electrons from four hydrogen atoms to form CH4. The one valence electron leaves sodium and adds to the seven valence electrons of chlorine to form the ionic formula unit NaCl (Figure 1a). Transition metals do not normally bond in this fashion. They primarily form coordinate covalent bonds, a...

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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Hexathienocoronenes: synthesis and self-organization.

Long Chen1, Sreenivasa R Puniredd, Yuan-Zhi Tan

  • 1Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany.

Journal of the American Chemical Society
|October 16, 2012
PubMed
Summary

Hexathienocoronenes (HTCs), a new class of organic semiconductors, exhibit tunable properties based on alkyl chain length. While stronger donors than related compounds, their thin-film transistor performance is moderate due to limited self-assembly.

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

Area of Science:

  • Organic electronics
  • Materials science
  • Semiconductor chemistry

Background:

  • Coronenes and thiophene-annelated analogs are key organic semiconductor building blocks.
  • Tuning molecular structure is crucial for controlling electronic properties and film morphology.

Purpose of the Study:

  • To synthesize and characterize novel hexathienocoronenes (HTCs).
  • To investigate the influence of alkyl chain length on HTC phase formation and electronic properties.
  • To evaluate HTC performance in organic thin-film transistors (OTFTs).

Main Methods:

  • Synthesis of tetrasubstituted hexathienocoronenes with hexyl and dodecyl chains.
  • X-ray diffraction and differential scanning calorimetry for phase behavior analysis.
  • Fabrication and characterization of organic thin-film transistors (OTFTs) via vacuum deposition.

Main Results:

  • Hexathienocoronenes (HTCs) were successfully synthesized and functionalized.
  • Phase formation strongly depends on the length of the attached alkyl chains.
  • HTCs demonstrate enhanced donor strength compared to existing thiophene-annelated coronenes.
  • Vacuum-deposited HTC films yield modest field-effect mobilities (0.002 cm(2) V(-1) s(-1)).

Conclusions:

  • Hexathienocoronenes represent a promising new class of organic semiconductors with tunable properties.
  • Further optimization of film deposition techniques is needed to improve charge transport in HTC-based devices.
  • The strong dependence on chain length offers a pathway for rational design of new organic electronic materials.