(E)-stilbene
From Wikipedia, the free encyclopedia
| (E)-Stilbene | |
|---|---|
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| IUPAC name | trans-1,2-diphenylethylene (E)-1,2-diphenylethene |
| Other names | (E)-stilbene; trans-stilbene |
| Identifiers | |
| CAS number | [103-30-0] |
| SMILES | C(=Cc1ccccc1)c2ccccc2 |
| Properties | |
| Molecular formula | C14H12 |
| Molar mass | 180.24928 g/mol |
| Appearance | Solid |
| Melting point |
122°C - 125°C |
| Boiling point |
305°C - 307°C |
| Solubility in water | practically insoluble |
| Hazards | |
| MSDS | External MSDS |
| NFPA 704 |
 1
1
0
|
| Flash point | >112°C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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(E)-Stilbene, is a diarylethene, that is a hydrocarbon consisiting of an trans ethene double bond substituted with an phenyl group on both carbon atoms of the double bond. The name stilbene was derived from the Greek word stilbos, which means shining
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[edit] Isomers
Stilbene exists as two possible isomers. The first is trans-1,2-diphenylethylene, called trans-stilbene. The second is cis-1,2-diphenylethylene, called cis-stilbene which is sterically hindered and less stable because the steric interactions force the aromatic rings out-of-plane and prevent conjugation [ref?]. Z-stilbene has a melting point of 5°C to 6°C, while (E)-stilbene melts around 125°C, illustrating the the two compounds are quite different.
[edit] Uses
- Stilbene is used in manufacture of dyes and optical brighteners, and also as a phosphor and a scintillator.
- Stilbene is one of the gain mediums used in dye lasers.
- Many stilbene derivates (stilbenoids) are present naturally in plants. An example is resveratrol and its cousin, pterostilbene.
[edit] Chemistry
- Stilbene will typically have the chemistry of an conjugated alkene, that is a diarylethene.
- Trans- and cis-stilbene can isomerizes that is interconvert under the influence of light.
