(Z)-Stilbene

(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 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1616739
ChEBI	CHEBI:36008 ;
ChEMBL	ChEMBL393702 ;
ChemSpider	4512351 ;
ECHA InfoCard	100.010.406
EC Number	211-445-7;
Gmelin Reference	4380
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
	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). verify (what is ?) 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.^[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.

References

^ "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.
^ Price, Charles C.; Berti, Giancarlo (5 March 1954) [21 Sep 1953]. "The polymerization of stilbene in boron fluoride etherate". Journal of the American Chemical Society. 76 (5): 1221. Bibcode:1954JAChS..76.1219P. doi:10.1021/ja01634a004. Abstracted from Berti, Giancarlo. (PhD). Notre Dame University. {{cite thesis}}: Missing or empty |title= (help)

[1] "cis-Stilbene". pubchem.ncbi.nlm.nih.gov. Retrieved 5 December 2021.

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

[3] Price, Charles C.; Berti, Giancarlo (5 March 1954) [21 Sep 1953]. "The polymerization of stilbene in boron fluoride etherate". Journal of the American Chemical Society. 76 (5): 1221. Bibcode:1954JAChS..76.1219P. doi:10.1021/ja01634a004. Abstracted from Berti, Giancarlo. (PhD). Notre Dame University. {{cite thesis}}: Missing or empty |title= (help)

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