Hexabenzocoronene
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AFM image of hexabenzocoronene
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Names | |||
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Preferred IUPAC name
Hexabenzo[bc,ef,hi,kl,no,qr]coronene | |||
Other names
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Identifiers | |||
3D model (
JSmol ) |
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ChemSpider | |||
PubChem CID
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UNII | |||
CompTox Dashboard (EPA)
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Properties | |||
C42H18 | |||
Molar mass | 522.606 g·mol−1 | ||
Appearance | dark yellow[1] | ||
Density | 1.54 g/cm3 (calc.)[1] | ||
-346.0·10−6 cm3/mol[2] | |||
Structure[1] | |||
monoclinic , P21/a
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a = 1.8431(3) nm, b = 0.5119(1) nm, c = 1.2929(2) nm α = 90°, β = 112.57(1)°, γ = 90°
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Formula units (Z)
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2 | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hexa-peri-hexabenzocoronene (HBC) is a polycyclic aromatic hydrocarbon with the molecular formula C42H18. It consists of a central coronene molecule, with an additional benzene ring fused between each adjacent pair of rings around the periphery. It is sometimes simply called hexabenzocoronene, however, there are other chemicals that share this less-specific name, such as hexa-cata-hexabenzocoronene.
Hexa-peri-hexabenzocoronene has been imaged by
Supramolecular structures
Various hexabenzocoronenes have been investigated in
Synthesis
Organic synthesis of a hexabenzocoronene starts with an Aldol condensation reaction of dibenzyl ketone with a benzil derivative to give a substituted cyclopentadienone. A Diels–Alder reaction with alkyne and subsequent expulsion of carbon monoxide gives a hexaphenylbenzene. The adjacent pairs of benzene rings undergo oxidative electrocyclic reactions and aromatization by oxidation by iron(III) chloride in nitromethane.
References
External links
Media related to Hexabenzocoronene at Wikimedia Commons