1,1,4,4-Tetraphenylbutadiene

Tetraphenyl butadiene

Names
Preferred IUPAC name 1,1′,1′′,1′′′-(Buta-1,3-diene-1,1,4,4-tetrayl)tetrabenzene
Other names TPB
Identifiers
CAS Number	1450-63-1  N
ChemSpider	66678  Y
ECHA InfoCard	100.014.468
EC Number	CY9040630
PubChem CID	74060
UNII	3J9DS4FWS7  Y
CompTox Dashboard (EPA)	DTXSID4061701
InChI 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 Y Key: KLCLIOISYBHYDZ-UHFFFAOYSA-N Y
Properties
Chemical formula	C28H22
Molar mass	358.484 g·mol−1
Appearance	White to yellow white needles
Density	1.079 g/cm3
Melting point	203.5 °C (398.3 °F; 476.6 K)
Solubility	soluble in ethanol, benzene, chloroform, acetic acid [1]
Hazards
GHS labelling: [2]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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)	2 0 0
Flash point	289 °C (552 °F; 562 K)
Safety data sheet (SDS)	Sigma-Aldrich
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

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]

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]}

Related compounds

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

References

1. Lide, David R. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, FL: CRC Press. pp. 3–526. ISBN   978-0-8493-0594-8.
2. "1,1,4,4-Tetraphenyl-1,3-butadiene". pubchem.ncbi.nlm.nih.gov. Retrieved 12 December 2021.
3. Kido, J.; Shionoya, H.; Nagai, K. (1995). "Single-layer white light-emitting organic electroluminescent devices based on dye-dispersed poly( N -vinylcarbazole)". Applied Physics Letters. 67 (16): 2281–2283. Bibcode:1995ApPhL..67.2281K. doi:10.1063/1.115126..
4. A. Orechoff (1914). "Über eine neue Synthese einiger Inden-Derivate" [New synthesis of some indene derivatives]. Berichte der Deutschen Chemischen Gesellschaft. 47: 89-95. doi:10.1002/cber.19140470114.
5. Burton, W. M; Powell, B. A (1973). "Fluorescence of Tetraphenyl-Butadiene in the Vacuum Ultraviolet". Applied Optics. 12 (1): 87–9. Bibcode:1973ApOpt..12...87B. doi:10.1364/AO.12.000087. PMID   20125234..
6. Wise, Donald Lee; Gary E. Wnek; Debra J. Trantolo; Thomas M. Cooper; Joseph D. Gresser (1998). Photonic Polymer Systems. CRC Press. p. 250. ISBN   978-0-8247-0152-9 . Retrieved 2009-06-02.
7. Wernick, Miles N.; John N. Aarsvold (2004). Emission Tomography. Academic Press. p. 374. ISBN   978-0-12-744482-6 . Retrieved 2009-06-02.