Pyrene
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- For other uses, see Pyrene (disambiguation).
| Pyrene | |
|---|---|
 |
|
| General | |
| Systematic name | pyrene |
| Other names | benzo(d,e,f)phenanthrene |
| Molecular formula | C16H10 |
| SMILES | C12=CC=C3C=CC=C4 C=CC(C2=C34)=CC=C1 |
| Molar mass | 202.25 g/mol |
| Appearance | colorless solid
(yellow impurities are often found at trace levels in many samples). |
| CAS number | [129-00-0] [1] |
| Properties | |
| Density and phase | 1.271 g/ml |
| Solubility in water | 0.135 mg/l |
| Melting point | 145-148 °C (418-421 K) |
| Boiling point | 404 °C (677 K) |
| Structure | |
| Crystal structure | ? |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | irritant |
| NFPA 704 |
0
1
0
|
| Flash point | non-flammable |
| R/S statement | R: 36/37/38-45-53 S: 24/25-26-36 |
| RTECS number | UR2450000 |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related PAHs | benzopyrene |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
|
Pyrene is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings, resulting in a large, flat aromatic system. Pyrene is a colorless solid. It forms during incomplete combustion of organic material and therefore can be isolated from coal tar along with a broad range of related compounds. Animal studies have shown pyrene is toxic to the kidneys and the liver.
Pyrene is used commercially to make dyes, pesticides, pharmaceuticals, and plastics. It is also a valuable molecular probe for fluorescence spectroscopy, having a high quantum yield and lifetime (0.65 and 410 nanosecond, respectively, in ethanol at 293K). Its fluorescence emission spectrum is very sensitive to the solvent's polarity, so pyrene has been used as a probe to determine solvent environments.
Pyrene adopts a dimeric structure, with molecules arranged in sandwiched pairs in order to form lattice units. This results in a high degree of symmetry, belonging to the C2h symmetry group.
[edit] External links
[edit] References
- Birks, J. B. (1969). Photophysics of Aromatic Molecules. London: Wiley.
- Valeur, B. (2002). Molecular Fluorescence: Principles and Applications. New York: Wiley-VCH.
- Birks, J.B. (1975). Eximers. london: Reports on Progress in Physics.
- Fetzer, J. C. (2000). The Chemistry and Analysis of the Large Polycyclic Aromatic Hydrocarbons. New York: Wiley.
Pyrene in Greek mythology is only known as the mother of Cycnus by Ares.
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