Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and (Z)-Stilbene: Difference between pages

{{More citations needed|date=November 2023}}

{{DISPLAYTITLE:(''Z'')-Stilbene}}

|Watchedfields = changed

|verifiedrevid = 477201195

|Name = (''Z'')-Stilbene

|ImageFile = Stilbene_cis_structure.svg

|ImageFile1 = (Z)-Stilbene-3D-spacefill.png

|ImageName1 = C=black, H=white

|ImageAlt1 = (Z)-Stilbene molecule

|IUPACName = ''cis''-1,2-Diphenylethylene

|PIN = (''Z'')-1,2-Diphenylethene

|OtherNames = ''cis''-Stilbene

|Section1={{Chembox Identifiers

|CASNo_Ref = {{cascite|correct|CAS}}

|CASNo = 645-49-8

|Beilstein = 1616739

|ChEMBL_Ref = {{ebicite|correct|EBI}}

|ChEMBL = 393702

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChEBI_Ref = {{ebicite|correct|EBI}}

|ChEBI = 36008

|ChemSpiderID = 4512351

|EC_number = 211-445-7

|Gmelin = 4380

|PubChem = 5356785

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = TTG5048Y3K

|InChI = 1/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11-

|InChIKey = PJANXHGTPQOBST-QXMHVHEDBW

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 1S/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11-

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = PJANXHGTPQOBST-QXMHVHEDSA-N

|SMILES = c2(\C=C/c1ccccc1)ccccc2

|Section2={{Chembox Properties

|C=14 | H=12

|Appearance = Liquid

|Solubility = Practically insoluble

|MeltingPtC = 5 to 6

|BoilingPtC = 307

|BoilingPt_notes = at 1 atm (82°C to 84°C at 0.4 mmHg)

}}

|Section7={{Chembox Hazards

| Hazards_ref=<ref>{{cite web |title=cis-Stilbene |url=https://pubchem.ncbi.nlm.nih.gov/compound/5356785#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=5 December 2021 |language=en}}</ref>

|GHSPictograms = {{GHS07}}

|GHSSignalWord = Warning

|HPhrases = {{H-phrases|315|319}}

|PPhrases = {{P-phrases|264|280|302+352|305+351+338|321|332+313|337+313|362}}

|ExternalSDS = [http://msds.chem.ox.ac.uk/ST/cis-stilbene.html Oxford MSDS] }}

}}

'''(''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 language|Greek]] word {{lang|grc|stilbos}}, which means shining.

==Isomers==

Stilbene exists as two possible isomers known as [[(E)-Stilbene|(''E'')-stilbene]] and (''Z'')-stilbene. (''Z'')-Stilbene is [[steric effects|sterically hindered]] and less stable because the steric interactions force the aromatic rings 43° out-of-plane and prevent [[conjugated system|conjugation]].<ref>{{cite book |last1=Eliel |first1=Ernest L. |authorlink1 =Ernest L. Eliel |last2=Wilen |first2=Samuel H. |title=Stereochemistry of Organic Compounds |date=1994 |publisher=John Wiley and Sons |isbn=0-471-01670-5 |pages=566–567}}</ref> (''Z'')-Stilbene has a melting point of {{convert|5|-|6|C}}, while (''E'')-stilbene melts around {{convert|125|C}}, illustrating that the two compounds are quite different.

==Uses==

* Stilbene is used in manufacture of [[dye]]s and [[optical brightener]]s, and also as a [[phosphor]] and a [[scintillator]].

* Stilbene is one of the [[gain medium]]s used in [[dye laser]]s.

==Properties==

* Stilbene will typically have the chemistry of a [[diarylethene]], a conjugated [[alkene#Reactions|alkene]].

* Stilbene can undergo [[photoisomerization]] under the influence of UV light.

* Stilbene can undergo [[stilbene photocyclization]], an [[intramolecular reaction]].

* (Z)-Stilbene can undergo [[electrocyclic reaction]]s.

==Natural occurrence==

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

==References==

{{Reflist}}

{{DEFAULTSORT:Stilbene, (Z)-}}

[[Category:Luminescence]]

[[Category:Fluorescent dyes]]

[[Category:Phosphors and scintillators]]

[[Category:Laser gain media]]

[[Category:Stilbenoids]]

[[Category:Phenyl compounds]]