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| Names | |
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| Preferred IUPAC name Tetracene[1] | |
| Other names Naphthacene Benz[b]anthracene 2,3-Benzanthracene Tetracyclo[8.8.0.03,8.012,17]octadeca-1,3,5,7,9,11,13,15,17-nonaene | |
| Identifiers | |
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3D model (JSmol) | |
| ChEBI | |
| ChemSpider |
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| ECHA InfoCard | 100.001.945 |
| UNII | |
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| Properties | |
| C18H12 | |
| Molar mass | 228.29 g/mol |
| Appearance | Yellow to orange solid |
| Melting point | 357 °C (675 °F; 630 K) |
| Boiling point | 436.7 °C (818.1 °F; 709.8 K) |
| Insoluble | |
| −168.0·10−6 cm3/mol | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Tetracene, also callednaphthacene, is apolycyclic aromatic hydrocarbon. It has the appearance of a pale orange powder. Tetracene is the four-ringed member of the series ofacenes.
Tetracene is a molecularorganic semiconductor, used inorganic field-effect transistors (OFETs) andorganic light-emitting diodes (OLEDs). Tetracene can be used as again medium indye lasers as asensitiser inchemoluminescence. Napthacene is the main component of thetetracycline class of antibiotics.
In 1884, W. Roser attempted to synthesize a compound called "Aethindiphtalyls" (literally "ethyne diphthalyl")[2] by heating 3 parts ofphthalic anhydride, 3 parts ofsuccinic acid and one part ofsodium acetate according toSiegmund Gabriel's procedure.[3] 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 1898, Gabriel and Ernst Leupold conducted a study on the byproduct and confirmed it was a new class of compound containing 4 rings.[4]
In the same document, Gabriel and Leupold reported their synthesis of tetracene by condensating two moles of phthalic anhydride with a mole of succinic acid into aquinone then reduced with zinc dust.[4][5] They named in naphthacene, likely asportmanteau ofnaphthalene andanthracene. Modern nomenclature for polyacenes, including tetracene, was introduced byErich Clar in 1939.[6][7] Clar also developed a new route to synthesize tetracene from theFriedel-Crafts acylation between phthalic anhydride andtetralin catalyzed byAlCl3,ZnCl2 andNaCl involvingClemmensen reduction, forming 5,12-dihydrotetracene then dehydrogenated bychloranil to form tetracene.[8]
GermanphysicistJan Hendrik Schön claimed to have developed an electrically pumped laser based on tetracene during his time atBell Labs (1997–2002). However, his results could not be reproduced, and this is considered to be ascientific fraud.[9]
In May 2007, Japanese researchers fromTohoku University andOsaka University reported an ambipolar light-emitting transistor made of a single tetracene crystal.[10] Ambipolar means that theelectric charge is transported by both positively chargedholes and negatively chargedelectrons.
In 2024, it was used to produce lower-energy excitations in solar cells in a process known assinglet fission. An interface layer between tetracene and silicon transfers them into the silicon layer, where most of their energy can be converted into electricity.[11]
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