1,1,4,4-Tetraphenylbutadiene

Chemical compound From Wikipedia, the free encyclopedia

1,1,4,4-tetraphenylbutadiene (TPB) is an organic compound with the formula (C6H5)2C=CHCH=C(C6H5)2. Other isomers are possible, but the term usually refers to the derivative of butadiene with two phenyl group on each of the terminal carbon atoms It is a white solid that has attracted some attention as an electroluminescent dye.[3]

Quick facts Names, Identifiers ...
Tetraphenyl butadiene
Names
Preferred IUPAC name
1,1′,1′′,1′′′-(Buta-1,3-diene-1,1,4,4-tetrayl)tetrabenzene
Other names
TPB
Identifiers
ChemSpider
ECHA InfoCard 100.014.468 Edit this at Wikidata
EC Number
  • CY9040630
UNII
  • InChI=1S/C28H22/c1-5-13-23(14-6-1)27(24-15-7-2-8-16-24)21-22-28(25-17-9-3-10-18-25)26-19-11-4-12-20-26/h1-22H checkY
    Key: KLCLIOISYBHYDZ-UHFFFAOYSA-N checkY
Properties
C28H22
Molar mass 358.484 g·mol−1
Appearance White to yellow white needles
Density 1.079 g/cm3
Melting point 203.5 Â°C (398.3 Â°F; 476.6 K)
Solubility soluble in ethanol, benzene, chloroform, acetic acid[1]
Hazards
GHS labelling:[2]
GHS07: Exclamation mark
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
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
Flash point 289 Â°C (552 Â°F; 562 K)
Safety data sheet (SDS) Sigma-Aldrich
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
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The compound was first prepared by double dehydration of the diol.[4]

It glows blue with an emission spectrum peak wavelength at 430 nm,[5] It is useful as a wavelength shifter.[6][7]

1,2,3,4-Tetraphenylbutadiene ((C6H5)CH=C(C6H5)C(C6H5)=CH(C6H5)) is also well-known.

References

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