1,2,3,4-Tetraphenylbutadiene

1,2,3,4Ph4diene.svg 110 px 1,1′,1′′,1′′′-[(1E,3E)-Buta-1,3-diene-1,2,3,4-tetrayl]tetrabenzene 635-438-7 4526743 635-438-7 5377766 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+ DAABVBOFAIYKNX-GPAWKIAZSA-N C1=CC=C(C=C1)/C=C(/C(=C/C2=CC=CC=C2)/C3=CC=CC=C3)\C4=CC=CC=C4 28 22 white solid 1.19 g/cm310.1107/S0365110X65003808 The crystal and molecular structure of cis , cis -1,2,3,4-tetraphenylbutadiene 1965 Karle I. L. Dragonette K. S. Acta Crystallographica 19 4 500–503 1965AcCry..19..500K 07 Warning 302 315 319 335 413 261 264 264+265 270 271 273 280 301+317 302+352 304+340 305+351+338 319 321 330 332+317 337+317 362+364 403+233 405 501 1,2,3,4-Tetraphenylbutadiene is an organic compound with the formula [(C6H5)CH\dC(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:10.1021/ja01504a021 Novel Heterocyclopentadienes. II 1960 Leavitt F. C. Manuel T. A. Johnson F. Matternas L. U. Lehman D. S. Journal of the American Chemical Society 82 19 5099–5102 1960JAChS..82.5099L 2 PhC\tCPh + 2 Li -> LiCPh\dCPh\sCPh\dCPhLi (Ph = C6H5) LiCPh\dCPh\sCPh\dCPhLi + 2 H2O -> PhCH\dCPh\sCPh\dCHPh + 2 LiOH 1,4-Dilithiobutadiene is a precursor to several metallacycles by salt metathesis reactions: LiCPh\dCPh\sCPh\dCPhLi + 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. 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. 10.1063/1.115126 Single-layer white light-emitting organic electroluminescent devices based on dye-dispersed poly( N -vinylcarbazole) 1995 Kido J. Shionoya H. Nagai K. Applied Physics Letters 67 16 2281–2283 1995ApPhL..67.2281K . References Category:Aromatic hydrocarbons Category:Phenyl compounds Category:Conjugated dienes