(Z)-Stilbene

November 2023 changed 477201195 (Z)-Stilbene Stilbene_cis_structure.svg (Z)-Stilbene-3D-spacefill.png C=black, H=white (Z)-Stilbene molecule cis-1,2-Diphenylethylene (Z)-1,2-Diphenylethene cis-Stilbene correct CAS 645-49-8 1616739 correct EBI 393702 correct chemspider correct EBI 36008 4512351 211-445-7 4380 5356785 correct FDA TTG5048Y3K 1/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11- PJANXHGTPQOBST-QXMHVHEDBW correct chemspider 1S/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11- correct chemspider PJANXHGTPQOBST-QXMHVHEDSA-N c2(\C=C/c1ccccc1)ccccc2 14 12 Liquid Practically insoluble 5 to 6 307 at 1 atm (82°C to 84°C at 0.4 mmHg) cis-Stilbene https://pubchem.ncbi.nlm.nih.gov/compound/5356785#section=Safety-and-Hazards pubchem.ncbi.nlm.nih.gov 5 December 2021 en 07 Warning 315 319 264 280 302+352 305+351+338 321 332+313 337+313 362 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 word grc 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.Eliel Ernest L. Ernest L. Eliel Wilen Samuel H. Stereochemistry of Organic Compounds 1994 John Wiley and Sons 0-471-01670-5 566–567 (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. 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.10.1021/ja01634a004 5 March 1954 The polymerization of stilbene in boron fluoride etherate Charles C. Price Giancarlo Berti Journal of the American Chemical Society 21 Sep 1953 76 5 1221 1954JAChS..76.1219P Abstracted from Giancarlo Berti Notre Dame University PhD Natural occurrence Many stilbene derivatives (stilbenoids) are present naturally in plants. An example is resveratrol and its cousin, pterostilbene. References Category:Luminescence Category:Fluorescent dyes Category:Phosphors and scintillators Category:Laser gain media Category:Stilbenoids Category:Phenyl compounds