Tetracene

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 1898, Gabriel and Ernst Leupold conducted a study on the byproduct and confirmed it was a new class of compound containing 4 rings.

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. They named in naphthacene, likely as portmanteau of naphthalene and anthracene. Modern nomenclature for polyacenes, including tetracene, was introduced by Erich Clar in 1939. 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.

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.

In May 2007, Japanese researchers from Tohoku University and Osaka University reported an ambipolar light-emitting transistor made of a single tetracene crystal. 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.

Notes

References

References

1. [[International Union of Pure and Applied Chemistry]]. (2014). "Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013". [[Royal Society of Chemistry.
2. (1884). "Ueber Phtalylderivate. II.". [[Chemische Berichte]].
3. (1877). "Ueber die Einwirkung von wasserentziehenden Mitteln auf Säureanhydride". Chemische Berichte.
4. {{Cite Q. Q59885357
5. (1898). "Transformations of Ethinediphthalide". Gurney & Jackson.
6. Clar, E.. (1964). "Polycyclic Hydrocarbons". Springer.
7. {{Cite Q. Q67223987
8. (1942). "Eine neue Synthese des Tetracens". Chemische Berichte.
9. Agin, Dan. (2007). "Junk Science: An Overdue Indictment of Government, Industry, and Faith Groups That Twist Science for Their Own Gain". Macmillan.
10. (2007). "Ambipolar Light-Emitting Transistors of a Tetracene Single Crystal". Advanced Functional Materials.
11. (2024-03-08). "University of Paderborn Researchers Use Hawk Supercomputer and Lean into Imperfection to Improve Solar Cell Efficiency".