Tetraphenylethylene

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.^[3] Tetraphenylethylene is used as a precursor to other organic compounds, often in the area of supramolecular chemistry.

Tetraphenylethylene

Names
Preferred IUPAC name 1,1′,1′′,1′′′-Ethenetetrayltetrabenzene
Other names 1,1,2,2-Tetraphenylethene Tetraphenylethylene
Identifiers
CAS Number	632-51-9 Y
3D model (JSmol)	Interactive image
Beilstein Reference	789087
ChemSpider	62645 N
ECHA InfoCard	100.010.164
PubChem CID	69437
UNII	MT243CE29P Y
CompTox Dashboard (EPA)	DTXSID1060895
InChI InChI=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 N Key: JLZUZNKTTIRERF-UHFFFAOYSA-N N 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 Key: JLZUZNKTTIRERF-UHFFFAOYAF
SMILES c1ccc(cc1)C(=C(c2ccccc2)c3ccccc3)c4ccccc4
Properties
Chemical formula	C26H20
Molar mass	332.446 g·mol−1
Appearance	yellow solid
Density	1.088 g/cm3
Melting point	224 to 225 °C (435 to 437 °F; 497 to 498 K)[1]
Boiling point	424 °C (795 °F; 697 K)[2]
Hazards
Flash point	206.2 °C (403.2 °F; 479.3 K)
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

Synthesis

Tetraphenylethylene can be synthesized from diphenyldichloromethane using copper as a halide acceptor:^[4]

(C₆H₅)₂CCl₂ + 4 Cu → (C₆H₅)₂C=C(C₆H₅)₂ + 4 CuCl

Nickel can be used in place of copper.^[5]