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Merck

138924

Sigma-Aldrich

Cyclooctatetraen

98%

Synonym(e):

[8]Annulene

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About This Item

Empirische Formel (Hill-System):
C8H8
CAS-Nummer:
Molekulargewicht:
104.15
Beilstein:
2496800
MDL-Nummer:
UNSPSC-Code:
12352103
PubChem Substanz-ID:
NACRES:
NA.23

Assay

98%

Form

liquid

Enthält

0.1% hydroquinone as inhibitor

Brechungsindex

n20/D 1.537 (lit.)

bp

142-143 °C (lit.)

mp (Schmelzpunkt)

−5-−3 °C (lit.)

Dichte

0.925 g/mL at 25 °C (lit.)

Lagertemp.

−20°C

SMILES String

C1=CC=CC=CC=C1

InChI

1S/C8H8/c1-2-4-6-8-7-5-3-1/h1-8H/b2-1-,3-1-,4-2-,5-3-,6-4-,7-5-,8-6-,8-7-

InChIKey

KDUIUFJBNGTBMD-BONZMOEMSA-N

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Allgemeine Beschreibung

Cyclooctatetraene (COT) is a nonaromatic 4n π-conjugated system with a non-planar tub-shaped geometry and potential energy surfaces at the ground state.
Cyclooctatetraene is an 8p electron system and has a triplet ground state if the p electrons are delocalized. It is antiaromatic hence highly unstable and reactive. It adopts a non-planar boat conformation to attain stability with alternating single and double bonds and hence behaves like a polyolefin.

Anwendung

  • Used in the synthesis of highly organic film for silicon surfaces to improve its chemical and physical properties.
  • Used in liquid state organic dye lasers.
  • Used as triplet state quencher to reduce dye blinking.
COT may be functionalized by two side groups which can be used as active anode materials for rechargeable batteries. High capacity and voltage organic cathodes may be developed by using COT that can be fused with carbon molecules.

Signalwort

Danger

Gefahreneinstufungen

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 3

Flammpunkt (°F)

71.6 °F - closed cup

Flammpunkt (°C)

22 °C - closed cup

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Kunden haben sich ebenfalls angesehen

Aromaticity and antiaromaticity in the low-lying electronic states of cyclooctatetraene.
Karadakov PB.
The Journal of Physical Chemistry A, 112(49), 12707-12713 (2008)
Tyson E Graber et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 37(38), 9116-9131 (2017-08-20)
Neuronal mRNAs can be packaged in reversibly stalled polysome granules before their transport to distant synaptic locales. Stimulation of synaptic metabotropic glutamate receptors (mGluRs) reactivates translation of these particular mRNAs to produce plasticity-related protein; a phenomenon exhibited during mGluR-mediated LTD.
Superposed Redox Chemistry of Fused Carbon Rings in Cyclooctatetraene-Based Organic Molecules for High-Voltage and High-Capacity Cathodes.
Zhao X, et al.
ACS Applied Materials & Interfaces, 10(3), 2496-2503 (2018)
About the Antiaromaticity of Planar Cyclooctatetraene I thank Jens Panitzky for the additional DFT calculations, and Professor Jay Siegel, La Jolla, CA, and Professor Otto Ermer, Cologne, for helpful comments.
Frank-Gerrit Klärner
Angewandte Chemie (International ed. in English), 40(21), 3977-3981 (2002-10-31)
Sarah Schols et al.
Chemphyschem : a European journal of chemical physics and physical chemistry, 10(7), 1071-1076 (2009-04-18)
Phosphorescence and delayed fluorescence of polyfluorene polymer films doped with cyclooctatetraene (COT) and anthracene are studied by means of time-resolved photoluminescence (PL) measurements. The occurrence of an anomalous nonvertical triplet energy transfer in solid conjugated polymer films is demonstrated for

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