Rubicene
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| ImageFile = Rubicene.svg
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| IUPACName = rubicene
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|Section1={{Chembox Identifiers
| Abbreviations =
| CASNo = 197-61-5
| CASNo_Ref = {{cascite|correct|CAS}}
| Beilstein = 1914846
| ChEBI = 33095
| ChemSpiderID = 60779
| EC_number = 205-899-5
| PubChem = 67454
| UNII = J3I9M3715F
| SMILES = C1=CC=C2C(=C1)C3=C4C2=C5C=CC=C6C5=C(C4=CC=C3)C7=CC=CC=C76
| StdInChI = 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
| StdInChIKey = FMKFBRKHHLWKDB-UHFFFAOYSA-N
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|Section2={{Chembox Properties
| C=26 | H=14
| Appearance = Red solid
| Density =
| MeltingPtC = 306
| MeltingPt_notes = {{cite book | author=化学大辞典編集委員会 | title=化学大辞典(縮刷版)9 | publisher=共立出版 | date=1964 | isbn=4-320-04015-5 | oclc=990794711 | language=ja |page=855}}
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| SolubleOther = Insoluble in ethanol and benzene
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|Section6={{Chembox Pharmacology
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|Section7={{Chembox Hazards
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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. It's synthesized from fluorenone by reduction of calcium or magnesium, or it can be obtained by reacting with dihalogenated diphenylanthracene as raw material.{{cite journal|journal=Synthesis|volume=50|issue=1|language=en|issn=0039-7881|date=Jan 2018|pages=134–138|doi=10.1055/s-0036-1588570|url=http://www.thieme-connect.de/DOI/DOI?10.1055/s-0036-1588570|title=Facile Synthesis of Rubicenes by Scholl Reaction|accessdate=2022-10-06|author=Masahiko Kawamura, Eiji Tsurumaki, Shinji Toyota|s2cid=103648683 |url-access=subscription}} It can also be obtained by reacting 9,10-diphenylanthracene and 3 parts of DDQ in dichloromethane in the presence of triflic acid.
References
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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 lang|de}}. Zeitschrift fuer Chemie, 1985. 25 (6): 222. {{issn|0044-2402}}.
- {{cite journal|journal=Tetrahedron|volume=38|issue=10|language=en|date=Jan 1982|pages=1389–1396|doi=10.1016/0040-4020(82)80218-4|url=https://linkinghub.elsevier.com/retrieve/pii/0040402082802184|title=Thermal reactivities of polynuclear aromatic hydrocarbons and alkyl derivatives|accessdate=2022-10-06|author=William C. Herndon|url-access=subscription}}
{{PAHs}}
Category:Polycyclic aromatic hydrocarbons
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