Coronene#Occurrence and synthesis
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| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 460107606
| ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Coronene 200.svg
| ImageFile1 = Coronene3D.png
| PIN = Coronene{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 206 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}
| OtherNames = [6]circulene
X1001757-9, superbenzene, cyclobenzene
|Section1={{Chembox Identifiers
| Abbreviations =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8761
| InChIKey = VPUGDVKSAQVFFS-UHFFFAOYAQ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C24H12/c1-2-14-5-6-16-9-11-18-12-10-17-8-7-15-4-3-13(1)19-20(14)22(16)24(18)23(17)21(15)19/h1-12H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VPUGDVKSAQVFFS-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 191-07-1
| EINECS = 205-881-7
| PubChem = 9115
| SMILES = c1cc2ccc3ccc4ccc5ccc6ccc1c7c2c3c4c5c67
| InChI=1/C24H12/c1-2-14-5-6-16-9-11-18-12-10-17-8-7-15-4-3-13(1)19-20(14)22(16)24(18)23(17)21(15)19/h1-12H
| RTECS =
| UNII = 7YY0X5XT1W
| MeSHName =
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 29863
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C19375
| Gmelin = 286459
| Beilstein = 658468
}}
|Section2={{Chembox Properties
| C=24 | H=12
| Density = 1.371 g/cm3Haynes, p. 3.128
| MeltingPtC = 437.3
| BoilingPtC = 525
| Solubility = 0.14 μg/LHaynes, p. 5.145
| SolubleOther = Very soluble: benzene, toluene, hexane,Bertarelli, Chiara. [http://home.dei.polimi.it/sampietr/ESO/OK-03-Bertaelli-lezione2.pdf Molecules for organic electronics: intermolecular interactions vs properties]. Dipartimento di Chimica, Politecnico di Milano
Chloroform (1 mmol·L−1){{cite journal|last1=Wang|first1=Chen|last2=Wang|first2=Jianlin|last3=Wu|first3=Na|last4=Xu|first4=Miao|last5=Yang|first5=Xiaomei|last6=Lu|first6=Yalin|last7=Zang|first7=Ling|title=Donor–acceptor single cocrystal of coronene and perylene diimide: molecular self-assembly and charge-transfer photoluminescence|journal=RSC Adv.|date=2017|volume=7|issue=4|pages=2382–2387|doi=10.1039/C6RA25447K|bibcode=2017RSCAd...7.2382W|doi-access=free}} and ethers, sparingly soluble in ethanol.
| Solvent =
| BandGap = 1.7 eVHaynes, p. 12.95
| LogP = 7.38Chemspider, https://legacy.chemspider.com/Chemical-Structure.8761.html
| MagSus = −243.3·10−6 cm3/mol
}}
|Section3={{Chembox Structure
| CrystalStruct = Monoclinic
| LattConst_a = 10.02 Å
| LattConst_b = 4.67 Å
| LattConst_c = 15.60 Å
| LattConst_beta = 106.7
| UnitCellFormulas = 2
| SpaceGroup = P21/n
| Dipole = 0 D
| PointGroup = D6h
}}
|Section4={{Chembox Thermochemistry
|Thermochemistry_ref = Haynes, p. 6.156
| DeltaHfus = 19.2 kJ/mol
}}
|Section7={{Chembox Hazards
| GHSPictograms = {{GHS08}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|371}}
| PPhrases = {{P-phrases|260|264|270|309+311|405|501}}
| MainHazards =
| NFPA-H = 2
| NFPA-F = 1
| NFPA-R = 0
| NFPA-S =
| FlashPt =
| AutoignitionPt =
| ExploLimits =
| PEL = }}
}}
Coronene (also known as superbenzene and cyclobenzene) is a polycyclic aromatic hydrocarbon (PAH) comprising seven peri-fused benzene rings.{{cite book | last = Fetzer | first = J. C. | title = The Chemistry and Analysis of the Large Polycyclic Aromatic Hydrocarbons | location = New York | publisher = Wiley | year = 2000 }} Its chemical formula is {{chem|C|24|H|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, most stable structure for coronene has only three isolated outer sextets as fully aromatic although superaromaticity would still be possible when these sextets are able to migrate into next ring.
Occurrence and synthesis
Coronene occurs naturally as the very rare mineral carpathite, characterized by flakes of pure coronene embedded in sedimentary rock. This mineral may be created from ancient hydrothermal vent activity.[https://web.archive.org/web/20060205175225/http://luminousminerals.com/karpatite.shtml Karpatite]. luminousminerals.com In earlier times this mineral was also called karpatite or pendletonite.[http://www.mindat.org/min-2162.html Carpathite]. mindat.org
The presence of coronene putatively formed from contact of magma with fossil fuel deposits has been used to argue that Permian-Triassic “Great Dying” event was caused by a greenhouse gas warming episode triggered by large-scale Siberian vulcanism.{{cite journal|doi=10.1130/G48022.1|title=Pulsed volcanic combustion events coincident with the end-Permian terrestrial disturbance and the following global crisis|journal=Geology|year=2020|last1=Kaiho|first1=Kunio|last2= Aftabuzzaman|first2=Md.|last3=Jones|first3=David S.|last4=Tian|first4=Li|volume=49|issue=3|pages=289–293|doi-access=free}}
Coronene is produced in the petroleum-refining process of hydrocracking, where it can dimerize to a fifteen ring PAH, trivially named "dicoronylene" . Centimeter-long crystals can be grown from a supersaturated solution of 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.{{cite journal|doi=10.1038/ncomms11555|pmid=27161600|pmc=4866376|title=An unforeseen polymorph of coronene by the application of magnetic fields during crystal growth|journal=Nature Communications|volume=7|pages=11555|year=2016|last1=Potticary|first1=Jason|last2=Terry|first2=Lui R.|last3=Bell|first3=Christopher|last4=Papanikolopoulos|first4=Alexandros N.|last5=Christianen|first5=Peter C. M.|last6=Engelkamp|first6=Hans|last7=Collins|first7=Andrew M.|last8=Fontanesi|first8=Claudio|last9=Kociok-Köhn|first9=Gabriele|last10=Crampin|first10=Simon|last11=Da Como|first11=Enrico|last12=Hall|first12=Simon R.|arxiv=1509.04120|bibcode=2016NatCo...711555P}}
Structure
File:Coronene crystals luminescence.jpg
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) or by phase transition from γ decreasing the temperature below 158 K.{{Cite journal|last1=Salzillo|first1=Tommaso|last2=Giunchi|first2=Andrea|last3=Masino|first3=Matteo|last4=Bedoya-Martínez|first4=Natalia|last5=Della Valle|first5=Raffaele Guido|last6=Brillante|first6=Aldo|last7=Girlando|first7=Alberto|last8=Venuti|first8=Elisabetta|year=2018|title=An Alternative Strategy to Polymorph Recognition at Work: The Emblematic Case of Coronene|journal=Crystal Growth & Design|volume=18|issue=9|pages=4869–4873|doi=10.1021/acs.cgd.8b00934|s2cid=105480632}} The structure containing two C-H groups on one benzene ring, so-called DUO, was analyzed by infrared spectroscopy.{{Cite journal|last1=Sasaki|first1=Tatsuya|last2=Yamada|first2=Yasuhiro |last3=Sato|first3=Satoshi |date=2018-09-18|title=Quantitative Analysis of Zigzag and Armchair Edges on Carbon Materials with and without Pentagons Using Infrared Spectroscopy |journal=Analytical Chemistry|volume=90|issue=18|pages=10724–10731|doi=10.1021/acs.analchem.8b00949|pmid=30079720|s2cid=51920955|issn=0003-2700}}
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Other uses
Coronene has been used in the synthesis of graphene. For example, coronene molecules evaporated onto a copper surface at 1000 degrees Celsius will form a graphene lattice which can then be transferred onto another substrate.{{cite journal |last1=Wan |first1=Xi |display-authors=et al. |date=2013 |title=Enhanced Performance and Fermi-Level Estimation of Coronene-Derived Graphene Transistors on Self-Assembled Monolayer Modified Substrates in Large Areas |publisher=ACS Publications |journal=The Journal of Physical Chemistry C |volume=117 |issue=9 |pages=4800–4807 |doi= 10.1021/jp309549z}}
See also
- Cyclooctadecanonaene, the compound consisting 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
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References
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Cited sources
{{Commons category|Coronene}}
- {{cite book |ref=Haynes| editor= Haynes, William M. | date = 2016| title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = CRC Press | isbn = 9781498754293}}
{{PAHs}}