Chemistry:1,2,3,4-Tetraphenylbutadiene

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1,2,3,4-Tetraphenylbutadiene is an organic compound with the formula [(C
6H
5)CH=C(C
6H
5)]
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:[1]

2 PhC≡CPh + 2 Li → LiCPh=CPh–CPh=CPhLi (Ph = C6H5)
LiCPh=CPh–CPh=CPhLi + 2 H
2O → PhCH=CPh–CPh=CHPh + 2 LiOH

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

LiCPh=CPh–CPh=CPhLi + RMCl
2 → Ph
4C
4MR + 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.[2]

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

  1. ↑ 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. doi:10.1021/ja01504a021. Bibcode: 1960JAChS..82.5099L. 
  2. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named Karle
  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. doi:10.1063/1.115126. Bibcode: 1995ApPhL..67.2281K. .



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