Tetraphenylethylene

Tetraphenylethylene
Names
	Preferred IUPAC name 1,1′,1′′,1′′′-Ethenetetrayltetrabenzene
	Other names 1,1,2,2-Tetraphenylethene; Tetraphenylethylene
Identifiers
CAS Number	632-51-9 ;
3D model (JSmol)	Interactive image ;
Beilstein Reference	789087
ChemSpider	62645 ;
ECHA InfoCard	100.010.164
PubChem CID	69437 ;
UNII	MT243CE29P ;
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 Key: JLZUZNKTTIRERF-UHFFFAOYSA-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)
Boiling point	424 °C (795 °F; 697 K)
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). verify (what is ?) Infobox references

Last updated May 26, 2025

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.

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]

References

↑ Banerjee, Moloy; Susanna J. Emond; Sergey V. Lindeman; Rajendra Rathore (2007). "Practical Synthesis of Unsymmetrical Tetraarylethylenes and Their Application for the Preparation of [Triphenylethylene−Spacer−Triphenylethylene] Triads" . The Journal of Organic Chemistry . 72 (21): 8054–8061. doi:10.1021/jo701474y. PMID 17880244.
↑ Lewis, Irwin C.; T. Edstrom (1963). "Thermal Reactivity of Polynuclear Aromatic Hydrocarbons". The Journal of Organic Chemistry . 28 (8): 2050–2057. doi:10.1021/jo01043a025.
↑ Hoekstra, A.; Vos, A. (1975). "The Crystal and Molecular Structures of Tetraphenylhydrazine and Related Compounds at –160°C. II. The Crystal Structures of Tetraphenylethylene (TPE) and Diphenylaminotriphenylmethane (DTM)". Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry. 31 (6): 1716–1721. Bibcode:1975AcCrB..31.1716H. doi:10.1107/S0567740875005973.
↑ Robert E. Buckles George M. Matlack (1951). "Tetraphenylethylene". Organic Syntheses . 31: 104. doi:10.15227/orgsyn.031.0104.
↑ Inaba, S (1982). "Metallic nickel as a reagent for the coupling of aromatic and benzylic halides". Tetrahedron Letters . 23 (41): 4215–4216. doi:10.1016/S0040-4039(00)88707-9.

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[Banerjee2007-1] Banerjee, Moloy; Susanna J. Emond; Sergey V. Lindeman; Rajendra Rathore (2007). "Practical Synthesis of Unsymmetrical Tetraarylethylenes and Their Application for the Preparation of [Triphenylethylene−Spacer−Triphenylethylene] Triads" . The Journal of Organic Chemistry . 72 (21): 8054–8061. doi:10.1021/jo701474y. PMID 17880244.

[Lewis1963-2] Lewis, Irwin C.; T. Edstrom (1963). "Thermal Reactivity of Polynuclear Aromatic Hydrocarbons". The Journal of Organic Chemistry . 28 (8): 2050–2057. doi:10.1021/jo01043a025.

[3] Hoekstra, A.; Vos, A. (1975). "The Crystal and Molecular Structures of Tetraphenylhydrazine and Related Compounds at –160°C. II. The Crystal Structures of Tetraphenylethylene (TPE) and Diphenylaminotriphenylmethane (DTM)". Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry. 31 (6): 1716–1721. Bibcode:1975AcCrB..31.1716H. doi:10.1107/S0567740875005973.

[4] Robert E. Buckles George M. Matlack (1951). "Tetraphenylethylene". Organic Syntheses . 31: 104. doi:10.15227/orgsyn.031.0104.

[Inaba1982-5] Inaba, S (1982). "Metallic nickel as a reagent for the coupling of aromatic and benzylic halides". Tetrahedron Letters . 23 (41): 4215–4216. doi:10.1016/S0040-4039(00)88707-9.

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