Tetracene

In 1884, W. Roser attempted to synthesize a compound called "Aethindiphtalyls" (literally "ethyne diphthalyl"){{cite journal |last1=Roser |first1=W. |title=Ueber Phtalylderivate. II. |journal=Chemische Berichte |date=1884 |volume=17 |issue=2 |pages=2770–2775 |doi=10.1002/cber.188401702230 |url=https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cber.188401702230| language= de|url-access=subscription }} by heating 3 parts of phthalic anhydride, 3 parts of succinic acid and one part of sodium acetate according to Siegmund Gabriel's procedure.{{cite journal |last1=Gabriel |first1=S. |first2=A. |last2=Michael |title=Ueber die Einwirkung von wasserentziehenden Mitteln auf Säureanhydride |journal= Chemische Berichte |date=1877 |volume=10 |issue=2 |pages=1559–1560 |doi=10.1002/cber.18770100271 |url= https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cber.18770100271 | language= de|url-access=subscription }} 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.{{Cite Q|Q59885357}}

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 a quinone then reduced with zinc dust.{{Cite journal |url= |title= Transformations of Ethinediphthalide |last1=Gabriel |first1=S. |last2= Leupold |first2= E.| work= Journal of the Chemical Society: Abstracts of Chemical Papers| page= [https://books.google.com/books?id=m8s1AQAAMAAJ&pg=RA3-PA482 482] |year=1898 |publisher= Gurney & Jackson |language=en}} They named in naphthacene, likely as portmanteau of naphthalene and anthracene. Modern nomenclature for polyacenes, including tetracene, was introduced by Erich Clar in 1939.{{cite journal |last=Clar |first=E. |title= Nomenclature of Polycyclic Hydrocarbons |date=1964 |work=Polycyclic Hydrocarbons: Volume 1 |pages=3–11 |editor= E. Clar |url= https://link.springer.com/chapter/10.1007/978-3-662-01665-7_1 |access-date=2024-11-11 |place=Berlin; Heidelberg |publisher=Springer |language=en |doi=10.1007/978-3-662-01665-7_1 |isbn=978-3-662-01665-7|url-access=subscription }}{{Cite Q|Q67223987}} Clar also developed a new route to synthesize tetracene from the Friedel-Crafts acylation between phthalic anhydride and tetralin catalyzed by AlCl₃, ZnCl₂ and NaCl involving Clemmensen reduction, forming 5,12-dihydrotetracene then dehydrogenated by chloranil to form tetracene.{{cite journal |last1=Clar |first1=E. |title=Eine neue Synthese des Tetracens |journal=Chemische Berichte |date=1942 |volume=75 |issue=10 |pages=1271–1273 |doi=10.1002/cber.19420751015| language= de}}

File:Erich Clar's Synthetic Route of Tetracene.svg

German physicist Jan Hendrik Schön claimed to have developed an electrically pumped laser based on tetracene during his time at Bell Labs (1997–2002). However, his results could not be reproduced, and this is considered to be a scientific fraud.{{cite book| last=Agin| first=Dan| title=Junk Science: An Overdue Indictment of Government, Industry, and Faith Groups That Twist Science for Their Own Gain| year= 2007| url=https://books.google.com/books?id=VxcjOL1j8iAC| publisher=Macmillan| isbn=978-0-312-37480-8 }}

In May 2007, Japanese researchers from Tohoku University and Osaka University reported an ambipolar light-emitting transistor made of a single tetracene crystal.{{cite journal |first1=T. |last1= Takahashi | first2=T. |last2= Takenobu |first3= J.| last3= Takeya |first4= Y. |last4= Iwasa |year=2007 |title=Ambipolar Light-Emitting Transistors of a Tetracene Single Crystal |url= http://www3.interscience.wiley.com/cgi-bin/abstract/114266185/ABSTRACT |url-status=dead |journal=Advanced Functional Materials |volume=17 |issue=10 |pages= 1623–1628 |doi=10.1002/adfm.200700046 |s2cid=135786504 |archive-url= https://archive.today/20121210110431/http://www3.interscience.wiley.com/cgi-bin/abstract/114266185/ABSTRACT |archive-date=2012-12-10|url-access=subscription }} Ambipolar means that the electric charge is transported by both positively charged holes and negatively charged electrons.

In 2024, it was used to produce lower-energy excitations in solar cells in a process known as singlet fission. An interface layer between tetracene and silicon transfers them into the silicon layer, where most of their energy can be converted into electricity.{{Cite press release |place= Paderborn University |first= |date= 2024-03-08 |title=University of Paderborn Researchers Use Hawk Supercomputer and Lean into Imperfection to Improve Solar Cell Efficiency |url= https://cleantechnica.com/2024/03/08/hawk-supercomputer-improves-solar-cell-efficiency/ |access-date=2024-03-10 |via= CleanTechnica.com |publisher= |language=en-US}}

• Tetraphene, also known as benz[a]anthracene
• Doxycycline

• {{cite news| last= Oberhaus| first= Daniel |url= https://www.wired.com/story/new-designs-could-boost-solar-cells-beyond-their-limits/ | title= New Designs Could Boost Solar Cells Beyond Their Limits| work= Wired| date= July 11, 2019}}

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Category:Polycyclic aromatic hydrocarbons

Category:Organic semiconductors

Category:Laser gain media

Category:Tetracyclic compounds

Category:Acenes