Tetraphenylethylene

Tetraphenylethene (TPE) is an organic chemical compound with the formula Ph2C=CPh2, where Ph = phenyl (C6H5). It has been described as a yellow solid, but single crystals are colorless. The molecule is crowded such that all four phenyl groups are twisted out of the plane defined by the center six carbon atoms.[3] Tetraphenylethene 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
3D model (JSmol)
789087
ChemSpider
ECHA InfoCard 100.010.164
UNII
  • 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
  • c1ccc(cc1)C(=C(c2ccccc2)c3ccccc3)c4ccccc4
Properties
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).
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Infobox references

Synthesis

Tetraphenylethene can be synthesized from diphenyldichloromethane.[4][5]

References
  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.
  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. doi:10.1107/S0567740875005973.
  4. 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.
  5. Robert E. Buckles George M. Matlack (1951). "Tetraphenylethylene". Organic Syntheses. 31: 104. doi:10.15227/orgsyn.031.0104.
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