CORONENE

Coronene is a highly symmetrical polycyclic aromatic hydrocarbon composed of seven fused benzene rings.
Coronene's extended π-electron system makes it valuable in fluorescence, spectroscopy, and organic semiconductor research.
Coronene is also widely studied as a model compound for graphene-like structures, nanocarbon materials, and PAH analysis.

CAS Number: 191-07-1
EC Number: 205-881-7
Molecular Formula: C24H12
Molecular Weight: 300.35 g/mol

Synonyms: CORONENE, 191-07-1, Hexabenzobenzene, superbenzene, Dibenzo(ghi,pqr)perylene, Dibenzo[ghi,pqr]perylene, 7YY0X5XT1W, NSC-90725, DTXSID5047740, CHEBI:29863, RefChem:579250, DTXCID5027724, 205-881-7, CCRIS 908, EINECS 205-881-7, C24H12, MFCD00004134, CORONENE (purity), NSC90725, Coronene 10 microg/mL in Acetonitrile, CS-W012132, SY051583, Coronene, BCR(R) certified Reference Material, Q420614, 1,12:4,5:8,9-Triethenotriphenylene,Dibenzo(ghi,pqr)perylene, Coronene; Circumbenzene; NSC 90725, NSC 90725, UNII-7YY0X5XT1W, Coronene, 97%, OL10162, CORONENE [IARC], CORONENE [MI], SCHEMBL26856, SCHEMBL510787, orb3023631, SCHEMBL1815373, SCHEMBL29363009, SCHEMBL29563511, MSK4361, Coronene (purified by sublimation), Coronene 10 |Ig/mL in Cyclohexane, Coronene, (purified by sublimation), Coronene 10 |Ig/mL in Acetonitrile, TN9379, Coronene 10 microg/mL in Cyclohexane, AKOS015840942, FC62148, ACETICACID2-ACETOXY-5-ACETYL-PH, Coronene, purified by sublimation, 99%, AS-56034, DB-002675, C1961, NS00004856, ST45022219, C19375, F448567, J-012345, 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/h1-12, 191-07-1, 205-881-7, 658468, [6]Circulene, Coronen, Coronene, Coronène, Coronene, Dibenzo[ghi,pqr]perylene, Hexabenzobenzo, superbenzene, Коронен, コロネン, 蒄, 16083-32-2, 80%, CORONENE (D12, 98%), Coronene, 1,2,3,4,5,6,7,8,9,10,11,12-dodecadehydro-, Coronene-d12, Dibenzo(ghi,pqr)perylene, EINECS 205-881-7, Hexabenzobenzene

Coronene is defined as a member of the all-benzenoid class of polycyclic aromatic hydrocarbons (PAHs) known as superbenzenes, characterized by a six-fold symmetry and belonging to the D6h point group.
Coronene serves as a framework for studying film formation and crystallization, and has applications in liquid crystals and organic semiconductors.

Coronene is a honeycomb shaped symmetric polycyclic aromatic hydrocarbons (PAHs) composed from six peri-fused adjacent benzene rings.
Coronene can be visualized as one central benzene fully enclosed by outer fused benzene rings.

Coronene is also known as cyclobenzene, superbenzene, or as a nanoflake fragment of graphene.
Coronene dissolves in common solvents such as toluene, benzene and dichloromethane.

When exposed to UV light, coronene solutions glow blue.
The high conjugation of coronene and its high intrinsic carrier mobility make it a great candidate for applications in organic electronics. 

Coronene is known as a superaromatic molecule with 24 π-electrons which does not conform to the 4n + 2 Huckel’s aromaticity rule.
RGB emission can be realized from three single-crystals that are composed only of coronene.
Yellow crystals of three-dimensional (3D) rod-crystal and one-dimensional (1D) wire-crystal exhibit different emission band under UV-light irradiation, blue and green, respectively, while the short and flat two-dimensional (2D) plate-crystal of coronene dimer exhibits red emission band.

Coronene is a ortho- and peri-fused polycyclic arene that consists of six peri-fused benzene rings.
Coronene is a polycyclic aromatic hydrocarbon (PAH) composed of seven fused benzene rings arranged in a highly symmetrical, planar structure.

Coronene is a crystalline aromatic compound known for its extended π-electron system, chemical stability, and characteristic fluorescence.
Coronene is mainly used in scientific research involving organic semiconductors, molecular electronics, spectroscopy, graphene-related materials, and studies of polycyclic aromatic hydrocarbons.

Coronene is one of over 100 different polycyclic aromatic hydrocarbons (PAHs).
PAHs are chemicals that are formed during the incomplete burning organic substances, such as fossil fuels.
They are usually found as a mixture containing two or more of these compounds.

Coronene is a polycyclic aromatic hydrocarbon (PAH) characterized by its large, planar structure composed of six fused benzene rings, forming a symmetrical, hexagonal shape.
Coronene's molecular formula is C24H12, and it has a molecular weight of approximately 300 g/mol.

Coronene is known for its high stability and strong fluorescence properties, making it of interest in various applications, including organic electronics and materials science.
Coronene exhibits a characteristic deep blue fluorescence when exposed to ultraviolet light.

Coronene is insoluble in water but soluble in organic solvents such as benzene and toluene.
Due to its aromatic nature, Coronene can participate in π-π stacking interactions, which are significant in the formation of solid-state materials.

Additionally, coronene has been studied for its potential role in environmental chemistry, particularly in relation to its occurrence in soot and its implications for air quality and health.
Coronene's CAS number is 191-07-1, which uniquely identifies this compound in chemical databases.

Coronene is a polycyclic aromatic hydrocarbon (PAH) comprising seven peri-fused benzene rings.
Coronene's chemical formula is C24H12.

Coronene is a yellow material that dissolves in common solvents including benzene, toluene, and dichloromethane.
Coronene's solutions emit blue light fluorescence under UV light.
Coronene has been used as a solvent probe, similar to pyrene.

Coronene is of theoretical interest to organic chemists because of its aromaticity.
Coronene 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 three isolated outer sextets as fully aromatic although superaromaticity would still be possible when these sextets are able to migrate into next ring.

Uses of Coronene:
Coronene is used primarily as a reference compound in polycyclic aromatic hydrocarbon (PAH) research and analytical chemistry.
Coronene is employed in fluorescence spectroscopy, photophysical studies, and investigations of aromatic π-electron systems.

Coronene is also studied as a model molecule for graphene-like carbon structures and nanocarbon materials.
In materials science, Coronene is used in research on organic semiconductors, molecular electronics, charge-transfer systems, and optoelectronic materials.

Coronene can serve as a standard in chromatographic and spectrometric methods for the identification and quantification of PAHs.
Coronene is additionally used in combustion, soot-formation, astrochemistry, and interstellar-molecule research because of its highly condensed aromatic structure.

Coronene is used to synthesize MBE-grown layered superconductors.
Coronene is a polycyclic aromatic hydrocarbon found in smoked fish and was examined for potential toxic and carcinogenic effects.

Coronene is used to ultraviolet phosphor for charge-coupled devices.
Coronene is used in the production of graphene and as an ultraviolet phosphor in charge-coupled devices.

Coronene can be used:
To synthesize active materials for organic photovoltaic and optoelectronic applications.
As ′nucleation seed′ to synthesize graphene by vapor deposition at low temperatures.
To build novel polycyclic aromatic molecular frameworks and architectures.

Incorporation of coronene as ′Carbon Dot′ for bioimaging applications has been reported.

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.

Properties of Coronene:
Coronene appears as a yellow powder.
Coronene is extremely insoluble in water but generally very soluble in non-polar solvents such as benzene, chloroform, hexane, and toluene.

Coronene forms needle-like crystals with a monoclinic structure.
Additionally, Coronene exhibits a slightly blue fluorescence.

Preparation of Coronene:
Coronene can be synthesized using the Diels-Alder reaction.
This involves reacting perylene with a dienophile, such as maleic anhydride, under high temperatures ranging from 200 to 250 °C, in the presence of a solvent like nitrobenzene.

The reaction forms an adduct with additional carbon units attached to the perylene core.
Coronene is then subjected to oxidative cyclodehydrogenation.

This step can be achieved using reagents like iron(III) trichloride in a solvent such as dichloromethane or nitromethane, or by heating with a strong acid like sulfuric acid.
The process fuses the rings, resulting in coronene.

Coronene is important to note that this process should only be performed by experienced chemists, as it involves hazardous substances and is relatively complex.

Occurrence and Synthesis of Coronene:
Coronene occurs naturally as the very rare mineral carpathite, characterized by flakes of pure coronene embedded in sedimentary rock.
Coronene may be created from ancient hydrothermal vent activity.
In earlier times this mineral was also called karpatite or pendletonite.

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.

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 (~2.5  mg/ml), which is slowly cooled (~0.04 K/min) from 328 K (55 °C) to 298 K (25 °C) over a period of 12 hours.

Structure of Coronene:
Coronene is a planar circulene.
Coronene 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 (~1 tesla) or by phase transition from γ decreasing the temperature below 158 K (−115 °C).
The structure containing two C–H groups on one benzene ring, so-called DUO, was analyzed by infrared spectroscopy.

History of Coronene:
In 1932, the German chemist Kurt Meyer became the first person to make synthetic coronene.

Stability and Reactivity of Coronene:

Chemical Stability:
Stable under normal ambient and recommended storage conditions.

Reactivity:
Generally low reactivity under normal conditions.

Conditions to Avoid:
Excessive heat, open flames, ignition sources, and dust formation.

Incompatible Materials:
Strong oxidizing agents.

Hazardous Decomposition Products:
Thermal decomposition or combustion may produce carbon monoxide, carbon dioxide, and irritating fumes.

Handling and Storage of Coronene:

Safe Handling:
Handle with adequate ventilation.
Avoid generating or inhaling dust and avoid contact with skin and eyes.
Wash thoroughly after handling.

Storage Conditions:
Store in a tightly closed container in a cool, dry, and well-ventilated area away from incompatible materials and ignition sources.

First Aid Measures of Coronene:

Inhalation:
Move the affected person to fresh air.
Obtain medical attention if symptoms develop or persist.

Skin Contact:
Wash thoroughly with soap and water.
Remove contaminated clothing.

Eye Contact:
Rinse cautiously with water for several minutes.
Remove contact lenses if easy to do and continue rinsing.

Ingestion:
Rinse mouth with water.
Do not induce vomiting unless directed by medical personnel.
Seek medical advice if unwell.

Firefighting Measures of Coronene:

Suitable Extinguishing Media:
Use dry chemical powder, carbon dioxide, foam, or water spray as appropriate for the surrounding fire.

Specific Hazards:
Combustion may generate carbon oxides and irritating smoke or fumes.

Protective Equipment:
Firefighters should wear self-contained breathing apparatus and appropriate protective clothing.

Accidental Release Measures of Coronene:

Personal Precautions:
Avoid dust formation and direct contact.
Ensure adequate ventilation and use suitable protective equipment.

Environmental Precautions:
Prevent material from entering drains, surface water, or soil.

Cleanup Methods:
Carefully sweep or collect the material without generating dust and place it in a suitable closed container for disposal.

Exposure Controls/Personal Protective of Coronene:

Engineering Controls:
Provide adequate general or local exhaust ventilation, especially where dust may be generated.

Eye Protection:
Wear safety glasses or chemical safety goggles.

Hand Protection:
Use suitable chemical-resistant protective gloves.

Skin Protection:
Wear appropriate protective clothing.

Respiratory Protection:
Use an appropriate particulate respirator where ventilation is insufficient or airborne dust may be present.

Hygiene Measures:
Wash hands thoroughly after handling and before eating, drinking, or smoking.

Identifiers of Coronene:
Empirical Formula (Hill Notation): C24H12
CAS Number: 191-07-1
Molecular Weight: 300.35
UNSPSC Code: 12352100
NACRES: NA.22
PubChem Substance ID: 24893062
EC Number: 205-881-7
Beilstein/REAXYS Number: 658468
MDL number: MFCD00004134
Assay: 97%
Form: powder

Product number: C0386
Purity / Analytical Method : >80.0% (HPLC)
Molecular formula / molecular weight: C 2 4 H 1 2 = 300.36 
Physical state (20 °C): Solid
Storage conditions : Room Temperature (Recommended in a cool and dark place, <15°C)
CAS RN: 191-07-1
Reaxys registration number: 658468
PubChem substance identifier: 87565515
SDBS: 1373
Merck Index (14): 2536
MDL number: MFCD00004134

CAS Number: 191-07-1
Beilstein Reference: 658468
ChEBI: CHEBI:29863
ChemSpider: 8761
ECHA InfoCard: 100.005.348
EC Number: 205-881-7
Gmelin Reference: 286459
KEGG: C19375
PubChem CID: 9115
UNII: 7YY0X5XT1W
CompTox Dashboard (EPA): DTXSID5047740
InChI: InChI=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
Key: VPUGDVKSAQVFFS-UHFFFAOYSA-N
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
Key: VPUGDVKSAQVFFS-UHFFFAOYAQ
SMILES: c1cc2ccc3ccc4ccc5ccc6ccc1c7c2c3c4c5c67

CAS No.: 191-07-1
Chemical Name: CORONENE
CBNumber: CB9154454
Molecular Formula: C24H12
Molecular Weight: 300.35
MDL Number: MFCD00004134

CAS DataBase Reference: 191-07-1(CAS DataBase Reference)
EWG's Food Scores: 1
FDA UNII: 7YY0X5XT1W
IARC: 3 (Vol. 32, Sup 7, 92) 1987
EPA Substance Registry System: Coronene (191-07-1)
UNSPSC Code: 12352103
NACRES: NA.23

CAS Number: 191-07-1
Full Name: Coronene
Synonyms: circulene, cyclobenzene
Chemical Formula: C24H12
Molecular Weight: 300.36 g/mol
Absorption: λab 310.1 nm, 327.2 nm, 342.7 nm (in TCB)
Fluorescence: λem 447 nm (in CF)
Classification/Family: Polycyclic aromatic hydrocarbons (PAHs), Organic electronics

CAS: 191-07-1
Molecular Formula: C24H12
Molecular Weight (g/mol): 300.36
MDL Number: MFCD00004134
InChI Key: VPUGDVKSAQVFFS-UHFFFAOYSA-N
PubChem CID: 9115
ChEBI CHEBI:29863
IUPAC Name: coronene
SMILES: C1=CC2=CC=C3C=CC4=CC=C5C=CC6=CC=C1C1=C2C3=C4C5=C61

Properties of Coronene:
Chemical formula: C24H12
Molar mass: 300.360 g·mol−1
Appearance: Yellow powder
Density: 1.371 g/cm3
Melting point: 437.3 °C (819.1 °F; 710.5 K)
Boiling point: 525 °C (977 °F; 798 K)
Solubility in water: 0.14 μg/L
Solubility: Very soluble: benzene, toluene, hexane
Chloroform (1 mmol L−1) and ethers, sparingly soluble in ethanol.
log P: 7.38
Band gap: 1.7 eV
Magnetic susceptibility (χ): −243.3×10−6 cm3/mol

Quality Segment: 100
assay: 97%
form: powder
bp: 525 °C (lit.)
mp: 428 °C (lit.)
SMILES string: c1cc2ccc3ccc4ccc5ccc6ccc1c7c2c3c4c5c67
InChI: 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
InChI key: VPUGDVKSAQVFFS-UHFFFAOYSA-N

Melting point: 428 °C (lit.)
Boiling point: 525 °C (lit.)
Density: 1.39
refractive index: 1.4800 (estimate)
Flash point: 6 °C
storage temp.: Sealed in dry,Room Temperature
solubility: Chloroform (Slightly), Methanol (Slightly)
form: Crystalline Powder
color: Yellow to greenish
Water Solubility: 0.1ug/L(25 ºC)
Merck: 14,2536
BRN: 658468
Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
InChI: 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
InChIKey: VPUGDVKSAQVFFS-UHFFFAOYSA-N
SMILES: c1cc2ccc3ccc4ccc5ccc6ccc1c7c2c3c4c5c67

Molecular Weight: 300.4 g/mol
XLogP3: 7.2
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Rotatable Bond Count: 0
Exact Mass: 300.093900383 Da
Monoisotopic Mass: 300.093900383 Da
Topological Polar Surface Area: 0 Ų
Heavy Atom Count: 24
Complexity: 376
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Specifications of Coronene:
Melting Point: 438°C to 440°C
Color: Green to Yellow
Boiling Point: 525°C
Infrared Spectrum: Authentic
Assay Percent Range: 95%
Quantity: 100 mg
Merck Index: 15, 2523
Formula Weight: 300.35
Percent Purity: 95%
Physical Form: Crystalline Powder
Chemical Name or Material: Coronene, 95%

Appearance: Light yellow to Brown powder to crystal
Purity (HPLC): min. 80.0 area%
NMR: confirm to structure

Structure of Coronene:
Crystal structure: Monoclinic
Space group: P21/n
Point group: D6h
Lattice constant: 
a = 10.02 Å, b = 4.67 Å, c = 15.60 Å
α = 90°, β = 106.7°, γ = 90°
Formula units (Z): 2
Dipole moment: 0 D

Thermochemistry of Coronene:
Enthalpy of fusion (ΔfH⦵fus): 19.2 kJ/mol

Names of Coronene:

Preferred IUPAC name:
Coronene

Other names:
circulene
X1001757-9, superbenzene, cyclobenzene