(Z)-Stilbene

(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.

(Z)-Stilbene

C=black, H=white
Names
IUPAC name cis-1,2-Diphenylethylene
Preferred IUPAC name (Z)-1,2-Diphenylethene
Other names cis-Stilbene
Identifiers
CAS Number	645-49-8 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1616739
ChEBI	CHEBI:36008 Y
ChEMBL	ChEMBL393702 Y
ChemSpider	4512351 Y
ECHA InfoCard	100.010.406
EC Number	211-445-7
Gmelin Reference	4380
PubChem CID	5356785
UNII	TTG5048Y3K Y
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- 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
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[1]
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319
Precautionary statements	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). Y verify (what is YN ?) Infobox references

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.^[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

• 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.
• In strong (protic) acid, cis-stilbene oligomerizes to a phenylmethylene chain capped by diphenylindane groups. The analogous trans compound doees not so react.^[3]

Natural occurrence

Many stilbene derivatives (stilbenoids) are present naturally in plants. An example is resveratrol and its cousin, pterostilbene.