(Z)-Stilbene
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Names | |
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IUPAC name
cis-1,2-Diphenylethylene
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Preferred IUPAC name
(Z)-1,2-Diphenylethene | |
Other names
cis-Stilbene
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.010.406 ![]() |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C14H12 | |
Molar mass | 180.250 g·mol−1 |
Appearance | Liquid |
Melting point | 5 to 6 °C (41 to 43 °F; 278 to 279 K) |
Boiling point | 307 °C (585 °F; 580 K) at 1 atm (82°C to 84°C at 0.4 mmHg) |
Practically insoluble | |
Hazards | |
Safety data sheet | Oxford MSDS |
R-phrases (outdated) | R36 R38 |
S-phrases (outdated) | S26 S36 |
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 | |
(Z)-Stilbene is a diarylethene, that is, a hydrocarbon consisting of a cis 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.
Isomers[]
Stilbene exists as two possible isomers known as (E)-stilbene and (Z)-stilbene. (Z)-Stilbene is sterically hindered and less stable because the steric interactions force the aromatic rings 43° out-of-plane and prevent conjugation.[1] (Z)-Stilbene has a melting point of 5–6 °C (41–43 °F), while (E)-stilbene melts around 125 °C (257 °F), illustrating that the two compounds are quite different.
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.
Properties[]
- Stilbene will typically have the chemistry of a diarylethene, a conjugated alkene.
- Stilbene can undergo photoisomerization under the influence of UV light.
- Stilbene can undergo stilbene photocyclization, an intramolecular reaction.
- (Z)-Stilbene can undergo electrocyclic reactions.
Natural Occurrence[]
Many stilbene derivatives (stilbenoids) are present naturally in plants. An example is resveratrol and its cousin, pterostilbene.
References[]
- ^ Eliel, Ernest L.; Wilen, Samuel H. (1994). Stereochemistry of Organic Compounds. John Wiley and Sons. pp. 566–567. ISBN 0-471-01670-5.
- Luminescence
- Fluorescent dyes
- Phosphors and scintillators
- Laser gain media
- Stilbenoids
- Phenyl compounds