(Z)-Stilbene

For the class of antioxidant compounds that share the same chemical skeleton see stilbenoids.

(Z)-Stilbene
IUPAC name cis-1,2-Diphenylethylene (Z)-1,2-Diphenylethene
Other names cis-Stilbene
Identifiers
CAS number	645-49-8 Y
PubChem	5356785
ChemSpider	4512351 Y
EC number	211-445-7
ChEBI	CHEBI:36008 Y
ChEMBL	CHEMBL393702 Y
Jmol-3D images	Image 1
SMILES c2(\C=C/c1ccccc1)ccccc2
InChI InChI=1S/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11- Y Key: PJANXHGTPQOBST-QXMHVHEDSA-N Y 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
Properties
Molecular formula	C14H12
Molar mass	180.25 g mol−1
Appearance	Liquid
Melting point	5-6 °C
Boiling point	82–84 °C at 0.4 mmHg
Solubility in water	Practically insoluble
Hazards
MSDS	Oxford MSDS
R-phrases	R36 R38
S-phrases	S26 S36
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 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 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.
• Many stilbene derivates (stilbenoids) are present naturally in plants. An example is resveratrol and its cousin, pterostilbene.

Chemistry

• 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.