Hexacene(ZZZDKE01) on:
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Hexacene is an aromatic compound consisting of six linearly-fused benzene rings. It is a blue-green, air-stable solid with low solubility.
Hexacene is one of a series of linear polycyclic molecules created by such aromatic ring fusions, a series termed acenes—the previous in the series being pentacene (with five fused rings) and the next being
Molecular graphics representation of the X-ray crystallographic structure determined for 6,15-bis(tri-t-butylsilylethynyl)hexacene
€”hexacene with bulky, protective substituents in the reactive 6- and 15- ring positions, see rotating graphic at base of page.
Sander-Wise Polycyclic Aromatic Hydrocarbon Structure Index entry for hexacene
NIST Special Publication 922.
heptacene
Heptacene is an organic compound and a polycyclic aromatic hydrocarbon and the seventh member of the acene or polyacene family of linear fused benzene rings. This compound has long been pursued by chemists because of its potential interest in elec ...
(with seven). It and other acenes and their derivatives have been investigated in potential applications related to organic semiconductors. Like larger acenes, hexacene is poorly soluble, but derivatives have been prepared with improved solubility. 6,15-Bis(tri-t-butylsilylethynyl)hexacene, which melts with decomposition at 96 °C.
Syntheses and structure
Hexacene has been the subject of many syntheses. One route entails by thermal decarbonylation of monoketone precursor.
Further reading
*First synthesis: **Marschalk, C. Linear hexacenes. Bull. Soc. Chim. Fr. 6, 1112–1121 (1939). ** ** *By dehydrogenation of ''hexacosahydrohexacene'' bypalladium on carbon
Palladium on carbon, often referred to as Pd/C, is a form of palladium used as a catalyst. The metal is supported on activated carbon to maximize its surface area and activity.
Uses Hydrogenation
Palladium on carbon is used for catalytic hydrog ...
*Isolation:
*By decarbonylation of a diketone precursor:
*Deoxygenation route:
External links
Molecular graphics representation of the X-ray crystallographic structure determined for 6,15-bis(tri-t-butylsilylethynyl)hexacene
€”hexacene with bulky, protective substituents in the reactive 6- and 15- ring positions, see rotating graphic at base of page.
Sander-Wise Polycyclic Aromatic Hydrocarbon Structure Index entry for hexacene
NIST Special Publication 922.
References
{{PAHs Organic semiconductors Acenes Polycyclic aromatic hydrocarbons