Perylene
| Perylene[1] | |
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Perylene |
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Other names
peri-Dinaphthalene; Perilene; Dibenz[de,kl]anthracene |
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| Identifiers | |
| CAS number | 198-55-0  |
| PubChem | 9142 |
| UNII | 5QD5427UN7  |
| KEGG | C19497 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C20H12 |
| Molar mass | 252.31 g mol−1 |
| Appearance | Brown solid |
| Melting point |
276-279 °C |
| Hazards | |
| S-phrases | S22 S24/25 |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Perylene or perilene is a polycyclic aromatic hydrocarbon with the chemical formula C20H12, occurring as a brown solid. It or its derivatives may be carcinogenic, and it is considered to be a hazardous pollutant. In cell membrane cytochemistry, perylene is used as a fluorescent lipid probe. It is the parent compound of a class of rylene dyes.
[edit] Emission
Perylene displays blue fluorescence. It is used as a blue-emitting dopant material in OLEDs, either pure or substituted. Perylene can be also used as an organic photoconductor. It has an absorption maximum at 434 nm, and as with all polycyclic aromatic compounds, low water solubility (1.2 x 10−5 mmol/L). Perylene has a molar absorptivity of 38,500 M−1cm−1 at 435.7 nm (about 6.5 μg is sufficient for absorbence of 1).
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Perylene dissolved in dichloromethane exposed to Long Wave UV Light
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Perylene dissolved in dichloromethane exposed to Short Wave UV Light
[edit] Structure
The perylene molecule consists of two naphthalene molecules connected by a carbon-carbon bond at the 1 and 8 positions on both molecules. All of the carbon atoms in perylene are sp2 hybridized. When drawing the structure of perylene, it is important not to represent the center ring as a fifth benzene ring. By doing so, this would depict two of the carbons as sp3 hybridized and fail to reflect the aromaticity of part of the molecule, and therefore its ability to fluoresce. The structure of perylene has been extensively studied by X-ray crystallography.[2]
[edit] References
- ^ Perylene at Sigma-Aldrich
- ^ Donaldson, D. M.; Robertson, J. M.; White, J. G. (1953). "The crystal and molecular structure of perylene". Proc. R. Soc. Lond. A Math. Phys. Sci. 220 (1142): 311–321. doi:10.1098/rspa.1953.0189. JSTOR 99329.
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