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(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 , 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. (''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 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 c ...
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(E)-Stilbene
(''E'')-Stilbene, commonly known as ''trans''-stilbene, is an organic compound represented by the condensed structural formula CHCH=CHCH. Classified as a diarylethene, it features a central ethylene moiety with one phenyl group substituent on each end of the carbon–carbon double bond. It has an (''E'') stereochemistry, meaning that the phenyl groups are located on opposite sides of the double bond, the opposite of its geometric isomer, ''cis''-stilbene. ''Trans''-stilbene occurs as a white crystalline solid at room temperature and is highly soluble in organic solvents. It can be converted to ''cis''-stilbene photochemically, and further reacted to produce phenanthrene. Stilbene was discovered in 1843 by the French chemist Auguste Laurent. The name "stilbene" is derived from the Greek word ''στίλβω'' (''stilbo''), which means "I shine", on account of the lustrous appearance of the compound. Isomers Stilbene exists as two possible stereoisomers. One is ''trans ...
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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 influence of light, these compounds can generally perform two kinds of reversible isomerizations: * E to Z isomerizations, most common for stilbenes (and azobenzenes). This process goes through an excited state energy minimum where the aromatic rings lie at 90° to each other. This conformation drops to the ground state and generally relaxes to trans and cis forms in a 1:1 ratio, thus the quantum yield for E-Z isomerization is very rarely greater than 0.5. *6π electrocyclizations of the Z form, leading to an additional bond between the two aryl functionalities and a disruption of the aromatic character of these groups.J. March, ''Advanced Organic Chemistry'', 4th ed. (1992). The quantum yield of this reaction is generally less than 0.1, and in m ...
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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 reversible process. Applications Photoisomerization of the compound retinal in the eye allows for vision. Photoisomerizable substrates have been put to practical use, for instance, in pigments for rewritable CDs, DVDs, and 3D optical data storage solutions. In addition, interest in photoisomerizable molecules has been aimed at molecular devices, such as molecular switches, molecular motors, and molecular electronics. Another class of device that uses the photoisomerization process is as an additive in liquid crystals to change their linear and nonlinear properties. Due to the photoisomerization is possible to induce a molecular reorientation in the liquid crystal bulk, which is used in holography, as spatial filter or optical switching. ...
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Laser Gain Media
A laser is a device that emits light through a process of optical amplification based on the stimulated emission of electromagnetic radiation. The word "laser" is an acronym for "light amplification by stimulated emission of radiation". The first laser was built in 1960 by Theodore H. Maiman at Hughes Research Laboratories, based on theoretical work by Charles Hard Townes and Arthur Leonard Schawlow. A laser differs from other sources of light in that it emits light which is ''coherent''. Spatial coherence allows a laser to be focused to a tight spot, enabling applications such as laser cutting and lithography. Spatial coherence also allows a laser beam to stay narrow over great distances (collimation), enabling applications such as laser pointers and lidar (light detection and ranging). Lasers can also have high temporal coherence, which allows them to emit light with a very narrow spectrum. Alternatively, temporal coherence can be used to produce ultrashort pulses of light w ...
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Phosphors And Scintillators
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 visible light, and cathodoluminescent substances which glow when struck by an electron beam (cathode rays) in a cathode-ray tube. When a phosphor is exposed to radiation, the orbital electrons in its molecules are excited to a higher energy level; when they return to their former level they emit the energy as light of a certain color. Phosphors can be classified into two categories: fluorescent substances which emit the energy immediately and stop glowing when the exciting radiation is turned off, and phosphorescent substances which emit the energy after a delay, so they keep glowing after the radiation is turned off, decaying in brightness over a period of milliseconds to days. Fluorescent materials are used in applications in which the ...
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Fluorescent Dyes
A fluorophore (or fluorochrome, similarly to a chromophore) is a fluorescent chemical compound that can re-emit light upon light excitation. Fluorophores typically contain several combined aromatic groups, or planar or cyclic molecules with several π bonds. Fluorophores are sometimes used alone, as a tracer in fluids, as a dye for staining of certain structures, as a substrate of enzymes, or as a probe or indicator (when its fluorescence is affected by environmental aspects such as polarity or ions). More generally they are covalently bonded to a macromolecule, serving as a marker (or dye, or tag, or reporter) for affine or bioactive reagents (antibodies, peptides, nucleic acids). Fluorophores are notably used to stain tissues, cells, or materials in a variety of analytical methods, i.e., fluorescent imaging and spectroscopy. Fluorescein, via its amine-reactive isothiocyanate derivative fluorescein isothiocyanate (FITC), has been one of the most popular fluorophores. From a ...
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Luminescence
Luminescence is spontaneous emission of light by a substance not resulting from heat; or "cold light". It is thus a form of cold-body radiation. It can be caused by chemical reactions, electrical energy, subatomic motions or stress on a crystal. This distinguishes luminescence from incandescence, which is light emitted by a substance as a result of heating. Historically, radioactivity was thought of as a form of "radio-luminescence", although it is today considered to be separate since it involves more than electromagnetic radiation. The dials, hands, scales, and signs of aviation and navigational instruments and markings are often coated with luminescent materials in a process known as "luminising". Types The following are types of luminescence: * Chemiluminescence, the emission of light as a result of a chemical reaction **Bioluminescence, a result of biochemical reactions in a living organism **Electrochemiluminescence, a result of an electrochemical reaction **Lyolumine ...
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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 (including blueberries), grape leaves and vines, and ''Pterocarpus marsupium'' heartwood. Safety and regulation Pterostilbene is considered to be a corrosive substance, is dangerous upon exposure to the eyes, and is an environmental toxin, especially to aquatic life. A randomized, double-blind, placebo-controlled of healthy human subjects given pterostilbene for 6–8 weeks, showed pterostilbene to be safe for human use at dosages up to 250 mg per day. Its chemical relative, resveratrol, received FDA GRAS status in 2007, and approval of synthetic resveratrol as a safe compound by the European Food Safety Authority (EFSA) in 2016. Pterostilbene differs from resveratrol by exhibiting increased bioavailability (80% compared to 20% in ...
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Resveratrol
Resveratrol (3,5,4′-trihydroxy-''trans''-stilbene) is a stilbenoid, a type of natural phenol, and a phytoalexin produced by several plants in response to injury or when the plant is under attack by pathogens, such as bacteria or fungi. Sources of resveratrol in food include the skin of grapes, blueberries, raspberries, mulberries, and peanuts. Although commonly used as a dietary supplement and studied in laboratory models of human diseases, there is no high-quality evidence that resveratrol improves lifespan or has a substantial effect on any human disease. Research Resveratrol has been studied for its potential therapeutic use, with little evidence of anti-disease effects or health benefits in humans. Cardiovascular disease There is no evidence of benefit from resveratrol in people who already have heart disease. A 2018 meta-analysis found no effect on systolic or diastolic blood pressure; a sub-analysis revealed a 2 mmHg decrease in systolic pressure only from res ...
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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 chalcones. Most stilbenoids are produced by plants, and the only known exception is the antihelminthic and antimicrobial stilbenoid, 2-isopropyl-5- ''E'')-2-phenylvinylenzene-1,3-diol, biosynthesized by the Gram-negative bacterium '' Photorhabdus luminescens.'' Chemistry Stilbenoids are hydroxylated derivatives of stilbene and have a C6–C2–C6 structure. They belong to the family of phenylpropanoids and share most of their biosynthesis pathway with chalcones. Under UV irradiation, stilbene and its derivatives undergo intramolecular cyclization, called stilbene photocyclization to form dihydrophenanthrenes. Oligomeric forms are known as oligostilbenoids. Types ;Aglycones * Piceatannol in the roots of Norway spruces * Pinosylvin is a fungal toxin protecting wood f ...
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Electrocyclic Reaction
In organic chemistry, an electrocyclic reaction is a type of pericyclic rearrangement where the net result is one pi bond being converted into one sigma bond or vice versa. These reactions are usually categorized by the following criteria: * Reactions can be either photochemical or thermal. * Reactions can be either ring-opening or ring-closing (electrocyclization). * Depending on the type of reaction (photochemical or thermal) and the number of pi electrons, the reaction can happen through either a conrotatory or disrotatory mechanism. * The type of rotation determines whether the cis or trans isomer of the product will be formed. Classical examples The Nazarov cyclization reaction is a named electrocyclic reaction converting divinylketones to cyclopentenones. A classic example is the thermal ring-opening reaction of 3,4-dimethylcyclobutene. The cis isomer exclusively yields whereas the trans isomer gives the trans,trans diene: This reaction course can be explained in a sim ...
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Intramolecular Reaction
Intramolecular in chemistry describes a process or characteristic limited within the structure of a single molecule, a property or phenomenon limited to the extent of a single molecule. Examples * intramolecular hydride transfer (transfer of a hydride ion from one part to another within the same molecule) * intramolecular hydrogen bond (a hydrogen bond formed between two functional groups of the same molecule) *cyclization of ω-haloalkylamines and alcohols to form the corresponding saturated nitrogen and oxygen heterocycles, respectively (an SN2 reaction within the same molecule) In intramolecular organic reactions, two reaction sites are contained within a single molecule. This creates a very high effective concentration (resulting in high reaction rates), and, therefore, many intramolecular reactions that would not occur as an intermolecular reaction between two compounds take place. Examples of intramolecular reactions are the Smiles rearrangement, the Dieckmann condensation ...
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