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Related Concept Videos

Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

4.5K
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...
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

3.3K
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.
3.3K
Aromatic Hydrocarbon Anions: Structural Overview01:18

Aromatic Hydrocarbon Anions: Structural Overview

4.5K
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...
4.5K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.5K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
2.5K
Polymer Classification: Crystallinity01:21

Polymer Classification: Crystallinity

4.3K
Unlike ionic or small covalent molecules, polymers do not form crystalline solids due to the diffusion limitations of their long-chain structures. However, polymers contain microscopic crystalline domains separated by amorphous domains.
Crystalline domains are the regions where polymer chains are aligned in an orderly manner and held together in proximity by intermolecular forces. For example, chains in the crystalline domains of polyethylene and nylon are bound together by van der Waals...
4.3K
Thermal Sigmatropic Reactions: Overview01:16

Thermal Sigmatropic Reactions: Overview

2.7K
Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in...
2.7K

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Orientational Transition in a Liquid Crystal Triggered by the Thermodynamic Growth of Interfacial Wetting Sheets
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Evidence for charge-trapping inducing polymorphic structural-phase transition in pentacene.

Masahiko Ando1, Tom B Kehoe, Makoto Yoneya

  • 1Central Research Laboratory, Hitachi, Ltd., 7-1-1 Omika, Ibaraki, 319-1292, Japan.

Advanced Materials (Deerfield Beach, Fla.)
|November 11, 2014
PubMed
Summary

Charge localization causes pentacene polymorph changes. Molecular dynamics and spectroscopy reveal disorder-induced Anderson localization in pentacene molecules, impacting their structure.

Keywords:
charge localizationdensity functional theoryin-situ Raman spectroscopymolecular dynamicspentacenepolymorph

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Area of Science:

  • Organic electronics
  • Materials science
  • Solid-state physics

Background:

  • Pentacene polymorphs exhibit distinct electronic properties.
  • Understanding charge carrier behavior is crucial for organic semiconductor performance.

Purpose of the Study:

  • Investigate trapped-charge-induced transformations in pentacene polymorphs.
  • Elucidate the role of molecular disorder in charge localization.

Main Methods:

  • In situ Raman spectroscopy for real-time observation.
  • Molecular dynamics simulations for atomic-level insights.
  • Quantum chemical calculations for electronic properties.

Main Results:

  • Observed transformation of pentacene polymorphs due to trapped charge.
  • Charge localization identified at the pentacene-interface.
  • Static intermolecular disorder along the long axis confirmed.
  • Calculations suggest disorder sufficient for Anderson-type localization.

Conclusions:

  • Trapped charge and molecular disorder are key factors in pentacene polymorph transformation.
  • Anderson localization significantly influences charge carrier behavior in pentacene.
  • Findings provide insights into charge dynamics in organic semiconductors.