(''Z'')-Stilbene is a

diarylethene Diarylethene is the general name of a class of chemical compounds that have aromatic functional groups bonded to each end of a carbon–carbon double bond. The simplest example is stilbene, which has two geometric isomers, E and Z. Under the influe ...

, that is, a

hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually fain ...

consisting of a cis

ethene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon–carbon double bonds). Ethy ...

double bond substituted with a

phenyl In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula , and is often represented by the symbol Ph (archaically φ) or Ø. The phenyl group is closely related to benzene and can be viewed as a benzene ...

group on both carbon atoms of the double bond. The name stilbene was derived from the

Greek Greek may refer to: Anything of, from, or related to Greece, a country in Southern Europe: *Greeks, an ethnic group *Greek language, a branch of the Indo-European language family **Proto-Greek language, the assumed last common ancestor of all kno ...

word , 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 Conjugation or conjugate may refer to: Linguistics *Grammatical conjugation, the modification of a verb from its basic form *Emotive conjugation or Russell's conjugation, the use of loaded language Mathematics *Complex conjugation, the change o ...

. (''Z'')-Stilbene has a melting point of , while (''E'')-stilbene melts around , illustrating that the two compounds are quite different.

Uses

* Stilbene is used in manufacture of

dye Juan de Guillebon, better known by his stage name DyE, is a French musician. He is known for the music video of the single "Fantasy Fantasy is a genre of speculative fiction that involves supernatural or Magic (supernatural), magical ele ...

s and

optical brightener Optical brighteners, optical brightening agents (OBAs), fluorescent brightening agents (FBAs), or fluorescent whitening agents (FWAs), are chemical compounds that absorb light in the ultraviolet and violet region (usually 340-370 nm) of the ...

s, and also as a

phosphor A phosphor is a substance that exhibits the phenomenon of luminescence; it emits light when exposed to some type of radiant energy. The term is used both for fluorescent or phosphorescent substances which glow on exposure to ultraviolet or ...

and a

scintillator A scintillator ( ) is a material that exhibits scintillation, the property of luminescence, when excited by ionizing radiation. Luminescent materials, when struck by an incoming particle, absorb its energy and scintillate (i.e. re-emit the ab ...

. * Stilbene is one of the

gain medium The active laser medium (also called a gain medium or lasing medium) is the source of optical gain within a laser. The gain results from the stimulated emission of photons through electronic or molecular transitions to a lower energy state from ...

s used in

dye laser A dye laser is a laser that uses an organic dye as the lasing medium, usually as a liquid solution. Compared to gases and most solid state lasing media, a dye can usually be used for a much wider range of wavelengths, often spanning 50 to 100 n ...

Properties

* Stilbene will typically have the chemistry of a

, a conjugated

alkene In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins. The Internationa ...

. * Stilbene can undergo

photoisomerization In chemistry, photoisomerization is a form of isomerization induced by photoexcitation. Both reversible and irreversible photoisomerizations are known for photoswitchable compounds. The term "photoisomerization" usually, however, refers to a rev ...

under the influence of UV light. * Stilbene can undergo stilbene photocyclization, an

intramolecular reaction In chemistry, intramolecular describes a Chemical process, process or characteristic limited within the Chemical structure, structure of a single molecule, a property or phenomenon limited to the extent of a single molecule. Relative rates In i ...

. * (Z)-Stilbene can undergo

electrocyclic reaction In organic chemistry, an electrocyclic reaction is a type of pericyclic reaction, pericyclic, rearrangement reaction, rearrangement reaction where the net result is one pi bond being converted into one sigma bond or vice versa. These reactions are ...

s. *In strong (protic) acid, ''cis''-stilbene oligomerizes to a phenylmethylene chain capped by diphenylindane groups. The analogous ''trans'' compound doees not so react. Abstracted from

Natural occurrence

Many stilbene derivatives (

stilbenoid Stilbenoids are hydroxylated derivatives of stilbene. They have a C6–C2–C6 structure. In biochemical terms, they belong to the family of phenylpropanoids and share most of their biosynthesis pathway with Chalconoid, chalcones. Most stilbenoids ...

s) are present naturally in plants. An example is

resveratrol Resveratrol (3,5,4′-trihydroxy-''trans''-stilbene) is a stilbenoid, a type of natural phenol or polyphenol and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacterium, ba ...

and its cousin,

pterostilbene Pterostilbene () (trans-3,5-dimethoxy-4-hydroxystilbene) is a stilbenoid chemically related to resveratrol. In plants, it serves a defensive phytoalexin role. Natural occurrence Pterostilbene is found in almonds, various ''Vaccinium'' berries ( ...

References

{{DEFAULTSORT:Stilbene, (Z)- Luminescence Fluorescent dyes Phosphors and scintillators Laser gain media Stilbenoids Phenyl compounds