|Preferred IUPAC name
3D model (JSmol)
|Molar mass||300.36 g·mol−1|
|Appearance||white or pale yellow powder|
|Melting point||437.3 °C (819.1 °F; 710.5 K) |
|Boiling point||525 °C (977 °F; 798 K) |
|Solubility||Very soluble: benzene, toluene, hexane,|
Chloroform (1 mmol·L−1) and ethers, sparingly soluble in ethanol.
|R-phrases (outdated)||R10 R20/21/22 |
a = 10.02 Å, b = 4.67 Å, c = 15.60 Å
α = 90°, β = 106.7°, γ = 90°
Formula units (Z)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Coronene (also known as superbenzene) is a polycyclic aromatic hydrocarbon (PAH) comprising six peri-fused benzene rings. Its chemical formula is C
12. It is a yellow material that dissolves in common solvents including benzene, toluene, and dichloromethane. Its solutions emit blue light fluorescence under UV light. It has been used as a solvent probe, similar to pyrene.
The compound is of theoretical interest to organic chemists because of its aromaticity. It can be described by 20 resonance structures or by a set of three mobile Clar sextets. In the Clar sextet case, the most stable structure for coronene has only the three isolated outer sextets as fully aromatic although superaromaticity would still be possible when these sextets are able to migrate into the next ring.
Occurrence and synthesis
Coronene occurs naturally as the very rare mineral carpathite, which is characterized by flakes of pure coronene embedded in sedimentary rock. This mineral may be created from ancient hydrothermal vent activity. In earlier times this mineral was also called karpatite or pendletonite.
Coronene is produced in the petroleum-refining process of hydrocracking, where it can dimerize to a fifteen ring PAH, trivially named "dicoronylene" (formally named benzo[10,11]phenanthro[2',3',4',5',6':4,5,6,7]chryseno[1,2,3-bc]coronene or benzo[1,2,3-bc:4,5,6-b'c']dicoronene). Centimeter-long crystals can be grown from a supersaturated solution of the molecules in toluene (ca. 2.5 mg/ml), which is slowly cooled (ca. 0.04 K/min) from 328 K to 298 K over a period of 12 hours.
Coronene is a planar circulene. It forms needle-like crystals with a monoclinic, herringbone-like structure. The most common polymorph is γ, but β form can also be produced in an applied magnetic field (ca. 1 Tesla).
- cyclooctadecanonaene, the compound consting of just the outer ring without the benzene core
- Hexa-peri-hexabenzocoronene and hexa-cata-hexabenzocoronene, consisting of additional benzene rings fused around the periphery
|Wikimedia Commons has media related to Coronene.|
- Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 206. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
- Coronene (EINECS NO. 205-881-7). guidechem.com
- Haynes, William M., ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). Boca Raton, FL: CRC Press. p. 3.128. ISBN 1439855110.
- Mackay, D.; Shiu, W. Y. (1977). "Aqueous solubility of polynuclear aromatic hydrocarbons". Journal of Chemical & Engineering Data. 22 (4): 399. doi:10.1021/je60075a012.
- Bertarelli, Chiara. Molecules for organic electronics: intermolecular interactions vs properties. Dipartimento di Chimica, Politecnico di Milano
- Wang, Chen; Wang, Jianlin; Wu, Na; Xu, Miao; Yang, Xiaomei; Lu, Yalin; Zang, Ling (2017). "Donor–acceptor single cocrystal of coronene and perylene diimide: molecular self-assembly and charge-transfer photoluminescence". RSC Adv. 7 (4): 2382–2387. doi:10.1039/C6RA25447K.
- Potticary, Jason; Terry, Lui R.; Bell, Christopher; Papanikolopoulos, Alexandros N.; Christianen, Peter C. M.; Engelkamp, Hans; Collins, Andrew M.; Fontanesi, Claudio; Kociok-Köhn, Gabriele; Crampin, Simon; Da Como, Enrico; Hall, Simon R. (2016). "An unforeseen polymorph of coronene by the application of magnetic fields during crystal growth". Nature Communications. 7: 11555. doi:10.1038/ncomms11555. PMC 4866376. PMID 27161600.
- Fetzer, J. C. (2000). The Chemistry and Analysis of the Large Polycyclic Aromatic Hydrocarbons. New York: Wiley.
- Karpatite. luminousminerals.com
- Carpathite. mindat.org