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Rubicene
Names
	IUPAC name rubicene
Identifiers
CAS Number	197-61-5 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1914846
ChEBI	CHEBI:33095;
ChemSpider	60779;
ECHA InfoCard	100.005.364
EC Number	205-899-5;
PubChem CID	67454;
UNII	J3I9M3715F;
CompTox Dashboard (EPA)	DTXSID00173364 ;
	InChI 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;
	SMILES C1=CC=C2C(=C1)C3=C4C2=C5C=CC=C6C5=C(C4=CC=C3)C7=CC=CC=C76;
Properties
Chemical formula	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). Infobox references

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

^ ^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.
^ ^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)

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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