Rubicene

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Rubicene
File:Rubicene.svg
Names
IUPAC name
rubicene
Identifiers
3D model (JSmol)
1914846
ChEBI
ChemSpider
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EC Number
  • 205-899-5
E number Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=1S/C26H14/c1-3-9-17-15(7-1)19-11-5-13-22-24-18-10-4-2-8-16(18)20-12-6-14-21(26(20)24)23(17)25(19)22/h1-14H
    Key: FMKFBRKHHLWKDB-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C3=C4C2=C5C=CC=C6C5=C(C4=CC=C3)C7=CC=CC=C76
Properties
C26H14
Molar mass 326.398 g·mol−1
Appearance Red solid
Melting point 306 °C (583 °F; 579 K) [1]
Solubility Insoluble in ethanol and benzene[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[1] It's synthesized from fluorenone by reduction of calcium or magnesium,[1] or it can be obtained by reacting with dihalogenated diphenylanthracene as raw material.[2] It can also be obtained by reacting 9,10-diphenylanthracene and 3 parts of DDQ in dichloromethane in the presence of triflic acid.[2]

References

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Further reading

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  • 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. Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value)..
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