1,2,3,4-Tetraphenylbutadiene

1,2,3,4-Tetraphenylbutadiene
Identifiers
CAS Number	635-438-7;
3D model (JSmol)	Interactive image;
ChemSpider	4526743;
ECHA InfoCard	100.163.327
EC Number	635-438-7;
PubChem CID	5377766;
	InChI InChI=1S/C28H22/c1-5-13-23(14-6-1)21-27(25-17-9-3-10-18-25)28(26-19-11-4-12-20-26)22-24-15-7-2-8-16-24/h1-22H/b27-21+,28-22+ Key: DAABVBOFAIYKNX-GPAWKIAZSA-N;
	SMILES C1=CC=C(C=C1)/C=C(/C(=C/C2=CC=CC=C2)/C3=CC=CC=C3)\C4=CC=CC=C4;
Properties
Chemical formula	C28H22
Molar mass	358.484 g·mol−1
Appearance	white solid
Density	1.19 g/cm3
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H335, H413
Precautionary statements	P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1,2,3,4-Tetraphenylbutadiene is an organic compound with the formula [(C₆H₅)CH=C(C₆H₅)]₂. It is a white solid.

The compound is prepared by reductive coupling of diphenylacetylene using lithium metal followed by hydrolysis of the resulting 1,4-dilithiobutadiene:^[2]

2 PhC≡CPh + 2 Li → LiCPh=CPh−CPh=CPhLi (Ph = C₆H₅)

LiCPh=CPh−CPh=CPhLi + 2 H₂O → PhCH=CPh−CPh=CHPh + 2 LiOH

1,4-Dilithiobutadiene is a precursor to several metallacycles by salt metathesis reactions:

LiCPh=CPh−CPh=CPhLi + RMCl₂ → Ph₄C₄MR + 2 LiCl (RM = PhP, PhAs, PhSb)

Structure

The isomer with mutually cis phenyl groups is common. According to X-ray crystallography, the phenyl groups are significantly rotated out of the plane of the 1,3-butadiene core.^[1]

Related compounds

1,1,4,4-Tetraphenylbutadiene is an isomer of 1,2,3,4-tetraphenylbutadiene with two phenyl group on each of the terminal carbon atoms of the diene. It has attracted some attention as an electroluminescent dye.^[3]

References

^ ^a ^b Karle, I. L.; Dragonette, K. S. (1965). "The crystal and molecular structure of cis , cis -1,2,3,4-tetraphenylbutadiene". Acta Crystallographica. 19 (4): 500–503. Bibcode:1965AcCry..19..500K. doi:10.1107/S0365110X65003808.
^ Leavitt, F. C.; Manuel, T. A.; Johnson, F.; Matternas, L. U.; Lehman, D. S. (1960). "Novel Heterocyclopentadienes. II". Journal of the American Chemical Society. 82 (19): 5099–5102. Bibcode:1960JAChS..82.5099L. doi:10.1021/ja01504a021.
^ 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..

[Karle-1] Karle, I. L.; Dragonette, K. S. (1965). "The crystal and molecular structure of cis , cis -1,2,3,4-tetraphenylbutadiene". Acta Crystallographica. 19 (4): 500–503. Bibcode:1965AcCry..19..500K. doi:10.1107/S0365110X65003808.

[2] Leavitt, F. C.; Manuel, T. A.; Johnson, F.; Matternas, L. U.; Lehman, D. S. (1960). "Novel Heterocyclopentadienes. II". Journal of the American Chemical Society. 82 (19): 5099–5102. Bibcode:1960JAChS..82.5099L. doi:10.1021/ja01504a021.

[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..

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