9,10-Bis(phenylethynyl)anthracene

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9,10-Bis(phenylethynyl)anthracene
9,10-bis(phenylethynyl)anthracene.svg
9,10-Bis(phenylethynyl)anthracene-3D-balls.png
Names
Preferred IUPAC name
9,10-Bis(phenylethynyl)anthracene
Other names
9,10-Bis(2-phenylethynyl)anthracene, BPEA
Identifiers
3D model (JSmol)
1891432
ChEBI
ChemSpider
ECHA InfoCard 100.030.178 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 233-210-8
PubChem CID
UNII
  • InChI=1S/C30H18/c1-3-11-23(12-4-1)19-21-29-25-15-7-9-17-27(25)30(28-18-10-8-16-26(28)29)22-20-24-13-5-2-6-14-24/h1-18H Yes check.svgY
    Key: ZHBOFZNNPZNWGB-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C30H18/c1-3-11-23(12-4-1)19-21-29-25-15-7-9-17-27(25)30(28-18-10-8-16-26(28)29)22-20-24-13-5-2-6-14-24/h1-18H
    Key: ZHBOFZNNPZNWGB-UHFFFAOYAU
  • C(#Cc1ccccc1)c4c2ccccc2c(C#Cc3ccccc3)c5ccccc45
Properties
C30H18
Molar mass 378.473 g/mol
AppearanceOrange needle crystals
Melting point 252 to 258 °C (486 to 496 °F; 525 to 531 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Irritant (Xi)
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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9,10-Bis(phenylethynyl)anthracene (BPEA) is an aromatic hydrocarbon with the chemical formula is C30H18. It displays strong fluorescence and is used as a chemiluminescent fluorophore with high quantum efficiency.

It is used in lightsticks as a fluorophor producing ghostly green light. It is also used as a dopant for organic semiconductors in OLEDs.


9,10-Bis(phenylethinyl)anthracen 9,10-Bis(phenylethinyl)anthracen.jpg
9,10-Bis(phenylethinyl)anthracen

The emission wavelength can be lowered by substituting the anthracene core by halogens or alkyls. 2-ethyl and 1,2-dimethyl substituted BPEAs are also in use.

See also

Related Research Articles

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<span class="mw-page-title-main">Polycyclic aromatic hydrocarbon</span> Hydrocarbon composed of multiple aromatic rings

A polycyclic aromatic hydrocarbon (PAH) is a class of organic compounds that is composed of multiple aromatic rings. The simplest representative is naphthalene, having two aromatic rings and the three-ring compounds anthracene and phenanthrene. PAHs are uncharged, non-polar and planar. Many are colorless. Many of them are found in coal and in oil deposits, and are also produced by the combustion of organic matter—for example, in engines and incinerators or when biomass burns in forest fires.

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<span class="mw-page-title-main">9,10-Diphenylanthracene</span> Chemical compound

9,10-Diphenylanthracene is a polycyclic aromatic hydrocarbon. It has the appearance of a slightly yellow powder. 9,10-Diphenylanthracene is used as a sensitiser in chemiluminescence. In lightsticks it is used to produce blue light. It is a molecular organic semiconductor, used in blue OLEDs and OLED-based displays.

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2-Chloro-9,10-bis(phenylethynyl)anthracene is a fluorescent dye used in lightsticks. It emits green light, used in 12-hour low-intensity Cyalume sticks.

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2-Chloro-9,10-diphenylanthracene is a fluorescent dye used in glow sticks for a blue-green glow. It is a chlorinated derivative of 9,10-diphenylanthracene.

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