| (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  |
| PubChem | 638088 |
| SMILES |
c2(\C=C\c1ccccc1)ccccc2
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| InChI |
1/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11+
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| InChI key | PJANXHGTPQOBST-VAWYXSNFBV |
| ChemSpider ID | 553649 |
| Properties | |
| Molecular formula | C14H12 |
| Molar mass | 180.25 g/mol |
| Appearance | Solid |
| Melting point |
122-125 °C |
| Boiling point |
305-307 °C |
| Solubility in water | Practically insoluble |
| Hazards | |
| MSDS | External MSDS |
| NFPA 704 |
 1
1
0
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| Flash point | >112 °C |
| (what is this?) (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
(E)-Stilbene, is a diarylethene, that is a hydrocarbon consisting of a trans ethene double bond substituted with a 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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Isomers
Stilbene exists as two possible isomers. The first is trans-1,2-diphenylethylene, called (E)-stilbene or trans-stilbene. The second is cis-1,2-diphenylethylene, called (Z)-stilbene or cis-stilbene, and is sterically hindered and less stable because the steric interactions force the aromatic rings out-of-plane and prevent conjugation[citation needed]. (Z)-Stilbene has a melting point of 5-6 °C, while (E)-stilbene melts around 125 °C, illustrating the two compounds are quite different in their physical properties.
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.
- Stilbene derivatives especially E(trans) isomer have estrogenic activity so used in making non-steroidal synthetic estrogens as Diethyl stilbestrol, Fosfosterol, Dienesterol.....
Chemistry
- Stilbene will typically have the chemistry of a conjugated alkene, that is a diarylethene.
- Trans- and cis-stilbene can interconvert under the influence of light.
External references
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