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Cyalume
Diphenyl oxalate (trademark name Cyalume) is a solid whose oxidation products are responsible for the chemiluminescence in a glowstick. This chemical is the double ester of phenol with oxalic acid. Upon reaction with hydrogen peroxide, 1,2-dioxetanedione is formed, along with release of the two phenols. The dioxetanedione then reacts with a dye molecule, decomposing to form carbon dioxide and leaving the dye in an excited state. As the dye relaxes back to its unexcited state, it releases a photon of visible light. : The reaction rate is pH dependent, and slightly alkaline conditions, achieved by adding a weak base, such as sodium salicylate, give a faster reaction and therefore produce brighter light. The TCPO, 2,4,6-trichlorophenol ester is a solid and thus easier to handle. Furthermore, since trichlorophenolate is the better leaving group, the reaction will proceed faster, again producing brighter light, as compared to the phenol ester. The following colors can be produced by us ...
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Glowstick
A glow stick, also known as a light stick, chem light, light wand, light rod, and rave light, is a self-contained, short-term light-source. It consists of a translucent plastic tube containing isolated substances that, when combined, make light through chemiluminescence. The light cannot be turned off and can be used only once. The used tube is then thrown away. Glow sticks are often used for recreation, such as for events, camping, outdoor exploration, and concerts. Glow sticks are also used for light in military and emergency services applications. Industrial uses include marine, transportation, and mining. History Bis(2,4,5-trichloro-6-(pentyloxycarbonyl)phenyl)oxalate, trademarked "Cyalume", was invented in 1971 by Michael M. Rauhut, of American Cyanamid, based on work by Edwin A. Chandross and David Iba Sr. of Bell Labs. Other early work on chemiluminescence was carried out at the same time, by researchers under Herbert Richter at China Lake Naval Weapons Center. Sever ...
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9,10-Bis(phenylethynyl)anthracene
9,10-Bis(phenylethynyl)anthracene (BPEA) is an aromatic hydrocarbon with the chemical formula is C30H18. It displays strong fluorescence and is used as a chemiluminescent fluorophore with high quantum efficiency. It is used in lightsticks as a fluorophor producing ghostly green light. It is also used as a dopant for organic semiconductors in OLEDs. The emission wavelength can be lowered by substituting the anthracene core by halogens or alkyls. 2-ethyl and 1,2-dimethyl substituted BPEAs are also in use. * 1-chloro-9,10-bis(phenylethynyl)anthracene emits yellow-green light, used in 30-minute high-intensity Cyalume sticks * 2-chloro-9,10-bis(phenylethynyl)anthracene emits green light, used in 12-hour low-intensity Cyalume sticks See also * Lightstick * Organic light-emitting diode * 5,12-Bis(phenylethynyl)naphthacene * 9,10-Diphenylanthracene 9,10-Diphenylanthracene is a polycyclic aromatic hydrocarbon. It has the appearance of a slightly yellow powder. 9,10-Diphenylanthrac ...
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1-Chloro-9,10-bis(phenylethynyl)anthracene
1-Chloro-9,10-bis(phenylethynyl)anthracene is a fluorescent dye used in lightsticks. It emits yellow-green light, used in 30-minute high-intensity Cyalume Diphenyl oxalate (trademark name Cyalume) is a solid whose oxidation products are responsible for the chemiluminescence in a glowstick. This chemical is the double ester of phenol with oxalic acid. Upon reaction with hydrogen peroxide, 1,2-dioxeta ... sticks. See also * 9,10-Bis(phenylethynyl)anthracene * 2-Chloro-9,10-bis(phenylethynyl)anthracene References Fluorescent dyes Organic semiconductors Anthracenes Alkyne derivatives Chloroarenes {{aromatic-stub ...
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Dimethyl Oxalate
Dimethyl oxalate is an organic compound with the formula or . It is the dimethyl ester of oxalic acid. Dimethyl oxalate is a colorless or white solid that is soluble in water. Production Dimethyl oxalate can be obtained by esterification of oxalic acid with methanol using sulfuric acid as a catalyst: :\rm 2\ CH_3OH + (CO_2H)_2\ \xrightarrow\ (CO_2CH_3)_2 + 2\ H_2O Oxidative carbonylation route The preparation by oxidative carbonylation has attracted interest because it requires only C1 precursors: :\rm 4 \ CH_3OH + 4 \ CO + O_2 \xrightarrow\ 2 \ (CO_2CH_3)_2 + 2 \ H_2O The reaction is catalyzed by Pd2+.E. Amadio''Oxidative Carbonylation of Alkanols Catalyzed by Pd(II)-Phosphine Complexes'' PhD Thesis, Ca'Foscari University Venice, 2009 The synthesis gas is mostly obtained from coal or biomass. The oxidation proceeds via dinitrogen trioxide, which is formed according to (1) of nitrogen monoxide and oxygen and then reacts according to (2) with methanol forming methyl nitrite: ...
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Sodium Salicylate
Sodium salicylate is a sodium salt of salicylic acid. It can be prepared from sodium phenolate and carbon dioxide under higher temperature and pressure. Historically, it has been synthesized by refluxing methyl salicylate (wintergreen oil) with an excess of sodium hydroxide. Properties Sodium salicylate is of the salicylate family. It is a shiny white powder with an aromatic flavor. Uses It is used in medicine as an analgesic and antipyretic. Sodium salicylate also acts as non-steroidal anti-inflammatory drug (NSAID), and induces apoptosis in cancer cells and also necrosis. It is also a potential replacement for aspirin for people sensitive to it. It may also be used as a phosphor for the detection of vacuum ultraviolet radiation and beta radiation A beta particle, also called beta ray or beta radiation (symbol β), is a high-energy, high-speed electron or positron emitted by the radioactive decay of an atomic nucleus, known as beta decay. There are two forms of beta decay, ...
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Oxalate Esters
Oxalate (systematic IUPAC name: ethanedioate) is an anion with the chemical formula . This dianion is colorless. It occurs naturally, including in some foods. It forms a variety of salt (chemistry), salts, for example sodium oxalate (), and several esters such as dimethyl oxalate (). It is a conjugate base of oxalic acid. At neutral pH in aqueous solution, oxalic acid converts completely to oxalate. Relationship to oxalic acid The dissociation of protons from oxalic acid proceeds in a determined order; as for other acid#Polyprotic acids, polyprotic acids, loss of a single proton results in the monovalent hydrogenoxalate anion . A salt (chemistry), salt with this anion is sometimes called an Acid salt, acid oxalate, monobasic oxalate, or hydrogen oxalate. The equilibrium constant (acid dissociation constant, ''K''a) for loss of the first proton is (pKa, p''K''a = 1.27). The loss of the second proton, which yields the oxalate ion, has an equilibrium constant of (p''K''a&n ...
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Rhodamine B
Rhodamine B is a chemical compound and a dye. It is often used as a tracer dye within water to determine the rate and direction of flow and transport. Rhodamine dyes fluorescence, fluoresce and can thus be detected easily and inexpensively with fluorometers. Rhodamine B is used in biology as a staining (biology), staining fluorescent dye, sometimes in combination with auramine O, as the auramine-rhodamine stain to demonstrate acid-fast organisms, notably ''Mycobacterium''. Rhodamine dyes are also used extensively in biotechnology applications such as Fluorescence microscope, fluorescence microscopy, flow cytometry, fluorescence correlation spectroscopy and ELISA. Other uses Rhodamine B is often mixed with herbicides to show where they have been used. It is also being tested for use as a Biomarker (medicine), biomarker in oral rabies vaccines for wildlife, such as raccoons, to identify animals that have eaten a vaccine bait (luring substance), bait. The rhodamine is incorporated ...
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Rhodamine 6G
Rhodamine 6G is a highly fluorescent rhodamine family dye. It is often used as a tracer dye within water to determine the rate and direction of flow and transport. Rhodamine dyes fluoresce and can thus be detected easily and inexpensively with instruments called fluorometers. Rhodamine dyes are used extensively in biotechnology applications such as fluorescence microscopy, flow cytometry, fluorescence correlation spectroscopy and ELISA. Forms Rhodamine 6G usually comes in three different forms. Rhodamine 6G chloride is a bronze/red powder with the chemical formula C28H31ClN2O3. Although highly soluble, this formulation is very corrosive to all metals except stainless steel. Other formulations are less soluble, but also less corrosive. Rhodamine 6G perchlorate (C28H31ClN2O7) comes in the form of red crystals, while rhodamine 6G tetrafluoroborate (C28H31BF4N2O3) appears as maroon crystals. Solubility Butanol (40 g/L), ethanol (80 g/L), methanol (400 g/L), pro ...
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Rubrene
Rubrene (5,6,11,12-tetraphenyltetracene) is the organic compound with the formula . It is a red colored polycyclic aromatic hydrocarbon. Because of its distinctive optical and electrical properties, rubrene has been extensively studied. It has been used as a sensitiser in chemoluminescence and as a yellow light source in lightsticks. Electronic properties As an organic semiconductor, the major application of rubrene is in organic light-emitting diodes (OLEDs) and organic field-effect transistors, which are the core elements of flexible displays. Single-crystal transistors can be prepared using crystalline rubrene, which is grown in a modified zone furnace on a temperature gradient. This technique, known as physical vapor transport, was introduced in 1998. Rubrene holds the distinction of being the organic semiconductor with the highest carrier mobility, reaching 40 cm2/(V·s) for holes. This value was measured in OFETs prepared by peeling a thin layer of single-crystall ...
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5,12-Bis(phenylethynyl)naphthacene
5,12-Bis(phenylethynyl)naphthacene is a fluorescent dye used in lightstick A glow stick, also known as a light stick, chem light, light wand, light rod, and rave light, is a self-contained, short-term light-source. It consists of a translucent plastic tube containing isolated substances that, when combined, make light ...s. It yields orange light. See also * 9,10-bis(phenylethynyl)anthracene References Fluorescent dyes Polycyclic aromatic hydrocarbons Organic semiconductors Alkyne derivatives {{Aromatic-stub ...
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Tetracene
Tetracene, also called naphthacene, is a polycyclic aromatic hydrocarbon. It has the appearance of a pale orange powder. Tetracene is the four-ringed member of the series of acenes. Tetracene is a molecular organic semiconductor, used in organic field-effect transistors (OFETs) and organic light-emitting diodes (OLEDs). Tetracene can be used as a gain medium in dye lasers as a sensitiser in chemoluminescence. Napthacene is the main component of the tetracycline class of antibiotics. History and synthesis In 1884, W. Roser attempted to synthesize a compound called "Aethindiphtalyls" (literally "ethyne diphthalyl") by heating 3 parts of phthalic anhydride, 3 parts of succinic acid and one part of sodium acetate according to Siegmund Gabriel's procedure. And then he found that there was a brick-red byproduct was produced in a large amount in the reaction, which was called "Isoäthindiphtalid" ("Isoethyne diphthalide") and founded to be an isomer of "Aethindiphtalyls". In 189 ...
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9,10-Diphenylanthracene
9,10-Diphenylanthracene is a polycyclic aromatic hydrocarbon. It has the appearance of a slightly yellow powder. 9,10-Diphenylanthracene is used as a sensitiser in chemiluminescence. In glow sticks it is used to produce blue light. It is a molecular organic semiconductor Organic semiconductors are solids whose building blocks are pi-bonded molecules or polymers made up by carbon and hydrogen atoms and – at times – heteroatoms such as nitrogen, sulfur and oxygen. They exist in the form of molecular crystals o ..., used in blue OLEDs and OLED-based displays. See also * 2-Chloro-9,10-diphenylanthracene, a chlorinated derivative References External links Polycyclic aromatic hydrocarbons Australian National Pollutant Inventory Organic semiconductors Anthracenes {{hydrocarbon-stub ...
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