Pyrene

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Pyrene
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Names
Preferred IUPAC name
Pyrene[1]
Other names
Benzo[def]phenanthrene
Identifiers
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3D model (JSmol)
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1307225
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84203
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  • InChI=1S/C16H10/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1-10H checkY
    Key: BBEAQIROQSPTKN-UHFFFAOYSA-N checkY
  • InChI=1/C16H10/c1-3-11-7-9-13-5-2-6-14-10-8-12(4-1)15(11)16(13)14/h1-10H
    Key: BBEAQIROQSPTKN-UHFFFAOYAB
  • c1cc2cccc3c2c4c1cccc4cc3
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°
4
Thermochemistry[8]
229.7 J/(K·mol)
224.9 J·mol−1·K−1
125.5 kJ·mol−1
Hazards
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NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point non-flammable
Related compounds
Related PAHs
 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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Template:Chembox Footer/trackingTemplate:Short description

Pyrene is a polycyclic aromatic hydrocarbon (PAH) with the formula Page Module:Chem2/styles.css has no content.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

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

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 Page Module:Chem2/styles.css has no content.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

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]

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STM image of self-assembled Br4Py molecules on Au(111) surface (top) and its model (bottom; pink spheres are Br atoms).[21]

Pyrene's fluorescence emission spectrum is very sensitive to solvent polarity.

Diagram showing the numbering and ring fusion locations of pyrene according to IUPAC nomenclature of organic chemistry.

Safety and environmental factors

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

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.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.
  2. ^ a b c Haynes, p. 3.472
  3. ^ Haynes, p. 5.162
  4. ^ Haynes, p. 5.176
  5. ^ Haynes, p. 12.96
  6. ^ Haynes, p. 3.579
  7. ^ Page Module:Citation/CS1/styles.css has no content.Camerman, A.; Trotter, J. (1965). "The crystal and molecular structure of pyrene". Acta Crystallographica. 18 (4): 636–643. doi:10.1107/S0365110X65001494.
  8. ^ Haynes, pp. 5.34, 6.161
  9. ^ GHS: PubChem
  10. ^ Page Module:Citation/CS1/styles.css has no content.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.
  11. ^ a b Senkan, Selim and Castaldi, Marco (2003) "Combustion" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim.
  12. ^ Page Module:Citation/CS1/styles.css has no content.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.
  13. ^ Page Module:Citation/CS1/styles.css has no content.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.
  14. ^ Page Module:Citation/CS1/styles.css has no content.Gumprecht, W. H. (1968). "3-Bromopyrene". Org. Synth. 48: 30. doi:10.15227/orgsyn.048.0030.
  15. ^ Page Module:Citation/CS1/styles.css has no content.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.
  16. ^ Page Module:Citation/CS1/styles.css has no content.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.
  17. ^ Page Module:Citation/CS1/styles.css has no content.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.
  18. ^ Page Module:Citation/CS1/styles.css has no content.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.
  19. ^ Page Module:Citation/CS1/styles.css has no content.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.
  20. ^ Page Module:Citation/CS1/styles.css has no content.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.
  21. ^ Page Module:Citation/CS1/styles.css has no content.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.
  22. ^ Page Module:Citation/CS1/styles.css has no content.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.
  23. ^ Page Module:Citation/CS1/styles.css has no content.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.
  24. ^ Page Module:Citation/CS1/styles.css has no content.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

Further reading

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