Rubicene - Misplaced Pages

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/h1-14HKey: 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
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 , 100 kPa). Infobox references

Chemical compound

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. 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

^ 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.
^ 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.

v t e Polycyclic aromatic hydrocarbons
2 rings	Butalene Azulene Naphthalene
3 rings	Acenaphthene Acenaphthylene Anthracene Fluorene Phenalene Phenanthrene
4 rings	Benzanthracene Benzofluorene Benzofluorene Benzophenanthrene Chrysene Fluoranthene Pyrene Tetracene Triphenylene Tricyclobutabenzene
5 rings	Benzacephenanthrylene Benzopyrene Benzopyrene Benzopyrene 6H-Benzopyrene(Olympicene) Benzofluoranthene Benzofluoranthene Benzofluoranthene Benzofluoranthene trans-Bicalicene Dibenzanthracene Dibenzanthracene Pentacene Pentaphene Perylene Picene Tetraphenylene
6 rings	Anthanthrene Benzoperylene Corannulene Dibenzopyrenes Hexacene Triangulene Zethrene
7+ rings	Coronene Dicoronylene Diindenoperylene Heptacene Hexabenzocoronene (Hexa-cata-) Kekulene Ovalene Rubicene Rubrene Sumanene Superphenalene Trinaphthylene Truxene
General classes	Acene Circulene Cyclacene Helicene Phenacene

This article about an aromatic compound is a stub. You can help Misplaced Pages by expanding it.