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(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.
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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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| 1616739 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.010.406 |
| EC Number |
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| 4380 | |
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[1] | |
| GHS labelling: | |
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| Warning | |
| H315, H319 | |
| P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362 | |
| Safety data sheet (SDS) | Oxford MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Isomers
editStilbene 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.[2] (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
edit- 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
edit- 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
editMany stilbene derivatives (stilbenoids) are present naturally in plants. An example is resveratrol and its cousin, pterostilbene.
References
edit- ^ "cis-Stilbene". pubchem.ncbi.nlm.nih.gov. Retrieved 5 December 2021.
- ^ Eliel, Ernest L.; Wilen, Samuel H. (1994). Stereochemistry of Organic Compounds. John Wiley and Sons. pp. 566–567. ISBN 0-471-01670-5.