Pyrene
Names | |
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Preferred IUPAC name
Pyrene[1] | |
Other names
Benzo[def]phenanthrene
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Identifiers | |
3D model (
JSmol ) |
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1307225 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.004.481 |
84203 | |
KEGG | |
PubChem CID
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RTECS number
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C16H10 | |
Molar mass | 202.256 g·mol−1 |
Appearance | colorless solid
(yellow impurities are often found at trace levels in many samples). |
Density | 1.271 g/cm3[2] |
Melting point | 150.62 °C (303.12 °F; 423.77 K)[2] |
Boiling point | 394 °C (741 °F; 667 K)[2] |
0.049 mg/L (0 °C) 0.139 mg/L (25 °C) 2.31 mg/L (75 °C)[3] | |
log P | 5.08[4] |
Band gap | 2.02 eV[5] |
-147·10−6 cm3/mol[6] | |
Structure[7] | |
Monoclinic
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P21/a | |
a = 13.64 Å, b = 9.25 Å, c = 8.47 Å α = 90°, β = 100.28°, γ = 90°
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Formula units (Z)
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4 |
Thermochemistry[8] | |
Heat capacity (C)
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229.7 J/(K·mol) |
Std molar
entropy (S⦵298) |
224.9 J·mol−1·K−1 |
Std enthalpy of (ΔfH⦵298)formation |
125.5 kJ·mol−1 |
Enthalpy of fusion (ΔfH⦵fus)
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17.36 kJ·mol−1 |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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irritant |
GHS labelling:[9] | |
Warning | |
H315, H319, H335, H410 | |
P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501 | |
NFPA 704 (fire diamond) | |
Flash point | non-flammable |
Related compounds | |
Related PAHs
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benzopyrene |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pyrene is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings, resulting in a flat aromatic system. The chemical formula is C16H10. This yellow-green solid is the smallest peri-fused PAH (one where the rings are fused through more than one face). Pyrene forms during incomplete combustion of organic compounds.[10]
Occurrence and properties
Pyrene was first isolated from coal tar, where it occurs up to 2% by weight. As a peri-fused PAH, pyrene is much more resonance-stabilized than its five-member-ring containing isomer fluoranthene. Therefore, it is produced in a wide range of combustion conditions. For example, automobiles produce about 1 μg/km.[11]
Reactions
Oxidation with
Reduction with sodium affords the radical anion. From this anion, a variety of pi-arene complexes can be prepared.[13]
Photophysics
Pyrene and its derivatives are used commercially to make dyes and dye precursors, for example pyranine and naphthalene-1,4,5,8-tetracarboxylic acid. It has strong absorbance in UV-Vis in three sharp bands at 330 nm in DCM. The emission is close to the absorption, but moving at 375 nm.[14] The morphology of the signals change with the solvent. Its derivatives are also valuable molecular probes via fluorescence spectroscopy, having a high quantum yield and lifetime (0.65 and 410 nanoseconds, respectively, in ethanol at 293 K). Pyrene was the first molecule for which excimer behavior was discovered.[15] Such excimer appears around 450 nm. Theodor Förster reported this in 1954.[16]
Applications
Pyrene's fluorescence emission spectrum is very sensitive to solvent polarity, so pyrene has been used as a probe to determine solvent environments. This is due to its excited state having a different, non-planar structure than the ground state. Certain emission bands are unaffected, but others vary in intensity due to the strength of interaction with a solvent.
Pyrenes are strong electron donor materials and can be combined with several materials in order to make electron donor-acceptor systems which can be used in energy conversion and light harvesting applications.[14]
Safety and environmental factors
Although it is not as problematic as
Its biodegradation has been heavily examined. The process commences with dihydroxylation at each of two kinds of CH=CH linkages.
See also
References
- ISBN 978-0-85404-182-4.
- ^ a b c Haynes, p. 3.472
- ^ Haynes, p. 5.162
- ^ Haynes, p. 5.176
- ^ Haynes, p. 12.96
- ^ Haynes, p. 3.579
- .
- ^ Haynes, pp. 5.34, 6.161
- ^ GHS: PubChem
- PMID 21740071.
- ^ a b Senkan, Selim and Castaldi, Marco (2003) "Combustion" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim.
- .
- PMID 25093352.
- ^ ISSN 2397-7132.
- .
- .
- PMID 24905327.
- .
- .
- .
- .
- PMID 19440284.
- PMID 6659544.
Cited sources
- Haynes, William M., ed. (2016). ISBN 9781498754293.
Further reading
- 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). "Excimers". Reports on Progress in Physics. 38 (8): 903–974. S2CID 240065177.
- Fetzer, J. C. (2000). The Chemistry and Analysis of the Large Polycyclic Aromatic Hydrocarbons. New York: Wiley.