(Z)-Stilbene

(Z)-Stilbene
Names


IUPAC names cis-1,2-Diphenylethylene (Z)-1,2-Diphenylethene
Other names cis-Stilbene
Identifiers
CAS Registry Number	645-49-8^Y
ChEBI	CHEBI:36008^Y
ChEMBL	ChEMBL393702^Y
ChemSpider	4512351^Y
EC number	211-445-7
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
Jmol-3D images	Image
PubChem	5356785
SMILES c2(\C=C/c1ccccc1)ccccc2
Properties
Molecular formula	C₁₄H₁₂
Molar mass	180.25 g·mol⁻¹
Appearance	Liquid
Melting point	5 to 6 °C (41 to 43 °F; 278 to 279 K)
Boiling point	82 to 84 °C (180 to 183 °F; 355 to 357 K) at 0.4 mmHg
Solubility in water	Practically insoluble
Hazards
MSDS	Oxford MSDS
R-phrases	R36 R38
S-phrases	S26 S36
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y verify (what is: Y/N?)
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. (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.
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.