Rubicene
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 A sample of rubicene | |
| Names | |
|---|---|
| IUPAC name
Rubicene | |
| Identifiers | |
3D model (JSmol) |
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| 1914846 | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.005.364 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C26H14 | |
| Molar mass | 326.398 g·mol−1 |
| Appearance | Red solid |
| Melting point | 306 °C (583 °F; 579 K) |
| Solubility | Insoluble in ethanol and benzene |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Rubicene is a polycyclic aromatic hydrocarbon that consists of two benzene and an anthracene. They are each linked by two carbon–carbon bonds. Dilute solutions of rubicene emit strong yellow fluorescence, while the solid compound is red. It's synthesized from fluorenone by reduction of calcium or magnesium, or it can be obtained by reacting with dihalogenated diphenylanthracene as raw material. It can also be obtained by reacting 9,10-diphenylanthracene and 3 parts of DDQ in dichloromethane in the presence of triflic acid.
References
- 1 2 3 4 化学大辞典編集委員会 (1964). 化学大辞典（縮刷版）9 (in Japanese). 共立出版. p. 855. ISBN 4-320-04015-5. OCLC 990794711.
{{cite book}}: ISBN / Date incompatibility (help) - 1 2 Masahiko Kawamura, Eiji Tsurumaki, Shinji Toyota (Jan 2018). "Facile Synthesis of Rubicenes by Scholl Reaction". Synthesis. 50 (1): 134–138. doi:10.1055/s-0036-1588570. ISSN 0039-7881. S2CID 103648683. Retrieved 2022-10-06.
{{cite journal}}: CS1 maint: multiple names: authors list (link)
Further reading
- Pragst, Fritz; Stoesser, Reinhard. Use of bis(1,2,4,6-tetramethyl-1,4-dihydro-4-pyridinyl) as a reducing agent for the generation of organic anion radicals in EPR spectroscopy (in German). Zeitschrift fuer Chemie, 1985. 25 (6): 222. ISSN 0044-2402.
- William C. Herndon (Jan 1982). "Thermal reactivities of polynuclear aromatic hydrocarbons and alkyl derivatives". Tetrahedron. 38 (10): 1389–1396. doi:10.1016/0040-4020(82)80218-4. Retrieved 2022-10-06.
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