(Z)-Stilbene

(Z)-Stilbene
Names
	IUPAC names cis-1,2-Diphenylethylene; (Z)-1,2-Diphenylethene
	Other names cis-Stilbene
Identifiers
CAS Number	645-49-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:36008 ;
ChEMBL	ChEMBL393702 ;
ChemSpider	4512351 ;
ECHA InfoCard	100.010.406
EC Number	211-445-7;
PubChem CID	5356785;
UNII	TTG5048Y3K ;
CompTox Dashboard (EPA)	DTXSID5026049 ;
	InChI InChI=1S/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11- Key: PJANXHGTPQOBST-QXMHVHEDSA-N ; InChI=1/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11- Key: PJANXHGTPQOBST-QXMHVHEDBW;
	SMILES c2(\C=C/c1ccccc1)ccccc2;
Properties
Chemical formula	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)
Solubility in water	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R-phrases (outdated)	R36 R38
S-phrases (outdated)	S26 S36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.

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References

Eliel, Ernest L.; Wilen, Samuel H. (1994). Stereochemistry of Organic Compounds. John Wiley and Sons. pp. 566–567. ISBN 0-471-01670-5.

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[1] Eliel, Ernest L.; Wilen, Samuel H. (1994). Stereochemistry of Organic Compounds. John Wiley and Sons. pp. 566–567. ISBN 0-471-01670-5.