tetraphenylethylene
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 420384835
| ImageFileL1 = Tetraphenylethylene.svg
| ImageSizeL1 = 150px
| ImageAltL1 =
| ImageFileR1 = File:Tetraphenylethylene-from-xtal-view-2-3D-bs-17.png
| ImageSizeR1 = 150px
| PIN = 1,1′,1′′,1′′′-Ethenetetrayltetrabenzene
| OtherNames = 1,1,2,2-Tetraphenylethene
Tetraphenylethylene
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 632-51-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = MT243CE29P
| PubChem =69437
| Beilstein = 789087
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 62645
| InChI = 1/C26H20/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22)26(23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H
| InChIKey = JLZUZNKTTIRERF-UHFFFAOYAF
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C26H20/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22)26(23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = JLZUZNKTTIRERF-UHFFFAOYSA-N
| SMILES = c1ccc(cc1)C(=C(c2ccccc2)c3ccccc3)c4ccccc4
}}
|Section2={{Chembox Properties
| C=26 | H=20
| MolarMass =
| Appearance = yellow solid
| Density = 1.088 g/cm3
| MeltingPtC = 224 to 225
| MeltingPt_ref = {{cite journal|last=Banerjee|first=Moloy|author2=Susanna J. Emond |author3=Sergey V. Lindeman |author4=Rajendra Rathore|authorlink4=Rajendra Rathore (chemist) |year=2007|title=Practical Synthesis of Unsymmetrical Tetraarylethylenes and Their Application for the Preparation of [Triphenylethylene−Spacer−Triphenylethylene] Triads|journal=The Journal of Organic Chemistry|volume=72|issue=21|pages=8054–8061|doi=10.1021/jo701474y|pmid=17880244|url=https://epublications.marquette.edu/chem_fac/625}}
| BoilingPtC = 424
| BoilingPt_ref = {{cite journal|last=Lewis|first=Irwin C.|author2=T. Edstrom |year=1963|title=Thermal Reactivity of Polynuclear Aromatic Hydrocarbons|journal=The Journal of Organic Chemistry|volume=28|issue=8|pages=2050–2057|doi=10.1021/jo01043a025}}
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPtC = 206.2
| AutoignitionPtC =
}}
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Tetraphenylethene (TPE) is an organic chemical compound with the formula Ph2C=CPh2, where Ph = phenyl (C6H5). Samples have been described as a yellow solid, but the compound iscolorless. The molecule is crowded such that all four phenyl groups are twisted out of the plane defined by the center six carbon atoms.{{cite journal |doi=10.1107/S0567740875005973|title=The Crystal and Molecular Structures of Tetraphenylhydrazine and Related Compounds at –160°C. II. The Crystal Structures of Tetraphenylethylene (TPE) and Diphenylaminotriphenylmethane (DTM) |year=1975 |last1=Hoekstra |first1=A. |last2=Vos |first2=A. |journal=Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry |volume=31 |issue=6 |pages=1716–1721 |bibcode=1975AcCrB..31.1716H }} Tetraphenylethylene is used as a precursor to other organic compounds, often in the area of supramolecular chemistry.
Synthesis
Tetraphenylethylene can be synthesized from diphenyldichloromethane using copper as a halide acceptor:{{cite journal |doi=10.15227/orgsyn.031.0104|title=Tetraphenylethylene |journal=Organic Syntheses |year=1951 |volume=31 |page=104|author=Robert E. Buckles George M. Matlack}}
:{{chem2|(C6H5)2CCl2 + 4 Cu -> (C6H5)2C\dC(C6H5)2 + 4 CuCl}}
Nickel can be used in place of copper.{{cite journal|last=Inaba|first=S|year=1982|title=Metallic nickel as a reagent for the coupling of aromatic and benzylic halides|journal=Tetrahedron Letters|volume=23|issue=41|pages=4215–4216|doi=10.1016/S0040-4039(00)88707-9}}
References
{{Reflist}}