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Rubicene

From Wikipedia, the free encyclopedia
Rubicene
Names
IUPAC name
rubicene
Identifiers
3D model (JSmol)
1914846
ChEBI
ChemSpider
ECHA InfoCard 100.005.364 Edit this at Wikidata
EC Number
  • 205-899-5
UNII
  • 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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  1. ^ a b c d 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.
  2. ^ a b 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

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