Pyrene
Pyrene is a polycyclic aromatic hydrocarbon (PAH) with the formula C16H10. Consisting of four fused benzene rings, it in a flat aromatic compound. This colorless compound 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.
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| 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 | 100.004.481 |
| 84203 | |
| KEGG | |
PubChem CID
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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 | |
| 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
formation (ΔfH⦵298) |
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] | |
 
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| 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) with the formula C16H10. Consisting of four fused benzene rings, it in a flat aromatic compound. This colorless compound 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
[edit]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
[edit]Pyrene contains two kinds of ring subunits: two a-rings with three CH bonds and two b-rings with two CH bonds.[12] The a-rings are more susceptible to reactions with electrophiles and oxidants. The b-rings can be partially hydrogenated to give tetrahydropyrene. Similarly the b-rings can be oxygenated to give the quinone-like derivative C16H8O2[13]
Oxidation with chromate affords perinaphthenone and then naphthalene-1,4,5,8-tetracarboxylic acid. Pyrene undergoes a series of hydrogenation reactions and is susceptible to halogenation, Diels-Alder additions, and nitration, all with varying degrees of selectivity.[11] Bromination occurs at one of the 1-positions.[14][15]
Reduction with sodium affords the radical anion. From this anion, a variety of pi-arene complexes can be prepared.[16]
Pyrene and its derivatives are used commercially to make dyes and dye precursors, for example pyranine and naphthalene-1,4,5,8-tetracarboxylic acid.
Photophysics
[edit]Pyrene has been described as "one of the most studied organic molecules in terms of its photophysical properties ..., by far, the most frequently applied dye in fluorescence labeled polymers". It is an electron donor in some donor-acceptor systems.[17] Its potential as a photocatalyst has also been heavily investigated.[18]
Pyrene was the first molecule for which excimer behavior was discovered.[19] Such excimer appears around 450 nm. Theodor Förster reported this in 1954.[20]
Pyrene's fluorescence emission spectrum is very sensitive to solvent polarityt.
Safety and environmental factors
[edit]Although it is not as problematic as benzopyrene, animal studies have shown pyrene is toxic to the kidneys and liver. It is now known that pyrene affects several living functions in fish and algae.[22]
Its biodegradation has been heavily examined. The process commences with dihydroxylation at each of two kinds of CH=CH linkages.[23] Experiments in pigs show that urinary 1-hydroxypyrene is a metabolite of pyrene, when given orally.[24]
See also
[edit]- List of interstellar and circumstellar molecules
- Perhydropyrene
- Fluoranthene, an isomeric PAH
References
[edit]- ^ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 206. doi:10.1039/9781849733069. 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
- ^ Camerman, A.; Trotter, J. (1965). "The crystal and molecular structure of pyrene". Acta Crystallographica. 18 (4): 636–643. doi:10.1107/S0365110X65001494.
- ^ Haynes, pp. 5.34, 6.161
- ^ GHS: PubChem
- ^ Figueira-Duarte, Teresa M.; Müllen, Klaus (2011). "Pyrene-Based Materials for Organic Electronics". Chemical Reviews. 111 (11): 7260–7314. doi:10.1021/cr100428a. PMID 21740071.
- ^ a b Senkan, Selim and Castaldi, Marco (2003) "Combustion" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim.
- ^ Wahab, Alexandra; Gershoni-Poranne, Renana (2025). "From Rings to Properties: Understanding the Effect of Annelation on Pyrene". The Journal of Organic Chemistry. 90 (36): 12667–12677. doi:10.1021/acs.joc.5c01401. PMC 12442067. PMID 40879728.
- ^ Casas-Solvas, Juan M.; Howgego, Joshua D.; Davis, Anthony P. (2014). "Synthesis of substituted pyrenes by indirect methods". Org. Biomol. Chem. 12 (2): 212–232. doi:10.1039/C3OB41993B. PMID 24276543.
- ^ Gumprecht, W. H. (1968). "3-Bromopyrene". Org. Synth. 48: 30. doi:10.15227/orgsyn.048.0030.
- ^ Matthias Schulze; Alexander Scherer; Colin Diner; Rik R. Tykwinski (2016). "Synthesis of 1-Bromopyrene and 1-Pyrenecarbaldehyde". Organic Syntheses. 93: 100–114. doi:10.15227/orgsyn.093.0100.
- ^ Kucera, Benjamin E.; Jilek, Robert E.; Brennessel, William W.; Ellis, John E. (2014). "Bis(pyrene)metal complexes of vanadium, niobium and titanium: Isolable homoleptic pyrene complexes of transition metals". Acta Crystallographica Section C: Structural Chemistry. 70 (8): 749–753. doi:10.1107/S2053229614015290. PMID 25093352.
- ^ Figueira-Duarte, Teresa M.; Müllen, Klaus (2011). "Pyrene-Based Materials for Organic Electronics". Chemical Reviews. 111 (11): 7260–7314. doi:10.1021/cr100428a. PMID 21740071.
- ^ Shan, Yiwei; Xu, Xinyu; Jin, Xingzhi; Ding, Xing; Wang, Shengyao; Chen, Hao (2025). "Review of Pyrene- and Perylene-Based Photocatalysts: Synthesis, Development, and Applications". Energy & Fuels. 39 (38): 18376–18405. doi:10.1021/acs.energyfuels.5c03751.
- ^ Van Dyke, David A.; Pryor, Brian A.; Smith, Philip G.; Topp, Michael R. (May 1998). "Nanosecond Time-Resolved Fluorescence Spectroscopy in the Physical Chemistry Laboratory: Formation of the Pyrene Excimer in Solution". Journal of Chemical Education. 75 (5): 615. Bibcode:1998JChEd..75..615V. doi:10.1021/ed075p615.
- ^ Förster, Th.; Kasper, K. (June 1954). "Ein Konzentrationsumschlag der Fluoreszenz". Zeitschrift für Physikalische Chemie. 1 (5_6): 275–277. doi:10.1524/zpch.1954.1.5_6.275.
- ^ Pham, Tuan Anh; Song, Fei; Nguyen, Manh-Thuong; Stöhr, Meike (2014). "Self-assembly of pyrene derivatives on Au(111): Substituent effects on intermolecular interactions". Chem. Commun. 50 (91): 14089–92. doi:10.1039/C4CC02753A. hdl:11370/5f1872e8-f225-4b4a-92f7-e56ad8b8a563. PMID 24905327.
- ^ Oliveira, M.; Gravato, C.; Guilhermino, L. (2012). "Acute toxic effects of pyrene on Pomatoschistus microps (Teleostei, Gobiidae): Mortality, biomarkers and swimming performance". Ecological Indicators. 19: 206–214. doi:10.1016/j.ecolind.2011.08.006.
- ^ Seo, Jong-Su; Keum, Young-Soo; Li, Qing (2009). "Bacterial Degradation of Aromatic Compounds". International Journal of Environmental Research and Public Health. 6 (1): 278–309. doi:10.3390/ijerph6010278. PMC 2672333. PMID 19440284.
- ^ Keimig, S. D.; Kirby, K. W.; Morgan, D. P.; Keiser, J. E.; Hubert, T. D. (1983). "Identification of 1-hydroxypyrene as a major metabolite of pyrene in pig urine". Xenobiotica. 13 (7): 415–20. doi:10.3109/00498258309052279. PMID 6659544.
Cited sources
[edit]- Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. ISBN 978-1-4987-5429-3.
Further reading
[edit]- 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. Bibcode:1975RPPh...38..903B. doi:10.1088/0034-4885/38/8/001. ISSN 0034-4885. S2CID 240065177.
- Fetzer, J. C. (2000). The Chemistry and Analysis of the Large Polycyclic Aromatic Hydrocarbons. New York: Wiley.
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