Heptacene

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Heptacene
Skeletal formula of heptacene
Space-filling model of the heptacene molecule
Names
Preferred IUPAC name
Heptacene
Identifiers
3D model (
JSmol
)
ChemSpider
UNII
  • InChI=1S/C30H18/c1-2-6-20-10-24-14-28-18-30-16-26-12-22-8-4-3-7-21(22)11-25(26)15-29(30)17-27(28)13-23(24)9-19(20)5-1/h1-18H
  • c1cc2cc3cc4cc5cc6cc7ccccc7cc6cc5cc4cc3cc2ccc1
Properties
C30H18
Molar mass 378.474 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[1] This compound has long been pursued by chemists[2][3][4] because of its potential interest in electronic applications and was first synthesized but not cleanly isolated in 2006.[5][6] Heptacene was finally fully characterized in bulk by researchers in Germany and the United States in 2017.[7]

heptacene synthesis
heptacene synthesis

The final step is a

dimers. When on the other hand the dione precursor is dissolved in a PMMA matrix first, heptacene can be studied by spectroscopy. Heptacene has been studied spectroscopically at cryogenic temperatures in a matrix.[8] When dissolved in sulfuric acid the heptacene dication is reported to be stable at room-temperature for more than a year in absence of oxygen.[9]
"[Isolated] solid heptacene has a half-life time of several weeks at room temperature."[10]

Derivatives

Figure 1.
Figure 2.

7,16-Bis(tris(trimethylsilyl)silylethynyl)heptacene was synthesized in 2005.[11] This compound is stable in the solid state for a week but decomposes in contact with air. Its synthesis started from anthraquinone and naphthalene-2,3-dicarboxaldehyde. More stable substituted heptacenes have been reported: with stabilizing p-(t-butyl)thiophenyl substituents (Figure 1)[12] and with phenyl and triisopropylsilylethynyl groups (Figure 2).[13]

References