TRIPHENYLENE

Triphenylene is a widely studied tertiary aromatic amine with a propeller-like molecular geometry and strong electron-rich character.
Triphenylene is commonly incorporated into organic semiconductors, electrochromic materials, and luminescent compounds to improve charge-transfer performance.
Triphenylene's structural versatility makes it especially useful for tailoring the optical and electronic behavior of advanced functional materials.

CAS Number: 217-59-4
EC Number: 205-922-9
Chemical Formula: C18H12
Molar Mass: 228.294 g/mol

Synonyms: TRIPHENYLENE, 217-59-4, 9,10-Benzophenanthrene, Isochrysene, 9,10-Benzphenanthrene, Benzo(l)phenanthrene, Benzo[l]phenanthrene, 1,2,3,4-Dibenznaphthalene, DTXSID9059757, NSC-57455, 18WX3373I0, CHEBI:33080, RefChem:191904, DTXCID7036537, 205-922-9, MFCD00001108, triphenylene (purity), 1,2:3,4-Dibenznaphthalene, 53814-75-8, triphenylen, CCRIS 1301, EINECS 205-922-9, NSC 57455, Triphenylene, 97%, Triphenylene, 98%, TRIPHENYLENE [MI], 1,3,4-Dibenznaphthalene, TRIPHENYLENE [IARC], SCHEMBL24104, SCHEMBL25597, SCHEMBL535021, SCHEMBL753619, orb2942855, SCHEMBL1666728, SCHEMBL2277041, SCHEMBL2284594, SCHEMBL2407351, SCHEMBL2407951, SCHEMBL2408225, SCHEMBL2408375, SCHEMBL2409495, SCHEMBL2409866, SCHEMBL2411457, SCHEMBL2411859, SCHEMBL2413265, SCHEMBL7531271, SCHEMBL7685672, CHEMBL1797416, SCHEMBL20300628, SCHEMBL29363356, SCHEMBL29698924, UNII-18WX3373I0, Triphenylene, analytical standard, MSK4358, ALBB-035099, NSC57455, STK368374, TN9795, AKOS004908298, Triphenylene (purified by sublimation), CS-W018431, FT33664, SB66862, Triphenylene 10 |Ig/mL in Cyclohexane, Triphenylene 10 |Ig/mL in Acetonitrile, AS-19089, SY019503, Triphenylene 10 microg/mL in Cyclohexane, Triphenylene 10 microg/mL in Acetonitrile, NS00026961, ST45021942, C19541, F364212, Triphenylene, BCR(R) certified Reference Material, Q2975866, InChI=1/C18H12/c1-2-8-14-13(7-1)15-9-3-4-11-17(15)18-12-6-5-10-16(14)18/h1-12

Triphenylene belongs to the class of polycyclic aromatic hydrocarbons, which is commonly employed as a substrate for use as a precursor for the synthesis of graphenes, carbon nanotubes, buckminsterfullerenes as well as polycyclic heteroaromatics.

Triphenylene is used in optics and electronics.
Triphenylene is also used as a discotic mesogen in liquid crystalline materials.

Further, Triphenylene is a compound that fluoresces in the ultraviolet region.
In addition to this, Triphenylene is used in the preparation of triphenylene-2-carbaldehyde.

Triphenylene is an ortho-fused polycyclic arene consisting of four fused benzene rings.

Triphenylene 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.

Triphenylene is an organic compound with the formula (C6H4)3.
Triphenylene is a flat polycyclic aromatic hydrocarbon (PAH) that has a highly symmetric and planar structure consists of four fused benzene rings.

Triphenylene has delocalized 18-π-electron systems based on a planar structure, corresponding to the symmetry group D3h.
Triphenylene is more resonance stable than its isomers chrysene, benz[a]anthracene, benzo[c]phenanthrene, and tetracene, hence resists hydrogenation.
Triphenylene is a light yellow powder, insoluble in water.

Triphenylene serves as a fundamental building block in discotic liquid crystals, where its planar, disc-like structure facilitates the formation of columnar mesophases, enabling applications in organic electronics.
Triphenylene's also being used as the base of covalent and metal organic frameworks.

Triphenylene is a polycyclic aromatic hydrocarbon consisting of four fused benzene rings arranged in a nonlinear fashion.
At room temperature, triphenylene exists as a colorless to pale yellow solid with a crystalline structure and exhibits minimal odor.
Triphenylene belongs to the class of aromatic hydrocarbons and demonstrates typical characteristics associated with this group, including chemical stability and limited solubility in polar solvents.

Triphenylene was first synthesized in the early 20th century during investigations into the structure and synthesis of complex aromatic compounds.
Triphenylene has been prepared via cyclodehydrogenation reactions involving suitable aromatic precursors under high-temperature conditions, often using transition metal catalysts such as nickel or palladium.

This synthetic route typically involves the dehydrogenative coupling of polyaromatic precursors to form the extended conjugated system characteristic of triphenylene.
Although primarily a laboratory-synthesized compound, trace amounts of triphenylene may occur in complex mixtures formed during the incomplete combustion of organic matter, such as in coal tar or soot.

In industrial settings, triphenylene finds use as a building block in the synthesis of larger polycyclic aromatic systems and as a model compound in studies related to graphene-like structures.
Additionally, Triphenylene has applications in materials science, particularly in the development of organic semiconductors and luminescent materials due to its rigid planar structure and favorable electronic properties.

Triphenylene is a polycyclic aromatic hydrocarbon (PAH) characterized by its planar structure consisting of four fused benzene rings, resulting in a highly symmetrical molecule.
Triphenylene has a molecular formula of C18H12 and is known for its distinct aromatic properties.

Triphenylene is typically a colorless solid at room temperature and exhibits a high melting point.
Triphenylene is insoluble in water but soluble in organic solvents such as benzene and toluene.

Triphenylene is notable for its fluorescence and has applications in organic electronics, particularly in organic light-emitting diodes (OLEDs) and as a host material in phosphorescent devices.
Additionally, triphenylene can participate in various chemical reactions, including electrophilic substitution, due to the presence of its aromatic rings.

Triphenylene's stability and unique electronic properties make it a subject of interest in materials science and nanotechnology.
However, like many PAHs, triphenylene is also scrutinized for its potential environmental and health impacts, as some PAHs are known to be carcinogenic.

Uses of Triphenylene:
Triphenylene is a polycyclic aromatic hydrocarbon (PAH) that can be isolated from coal tar.
Triphenylene emits fluorescence in the ultraviolet region and is a useful compound for developing semiconductor devices.

Triphenylene is used in optics and electronics.
Triphenylene is also used as a discotic mesogen in liquid crystalline materials.

Further, Triphenylene is a compound that fluoresces in the ultraviolet region.
In addition to this, Triphenylene is used in the preparation of triphenylene-2-carbaldehyde.

Applications of Triphenylene:
Triphenylene is an important basic skeleton monomer of polycyclic aromatic hydrocarbons.
Triphenylene can be used to synthesize macromolecular compounds with multi-conjugated structure, and is widely used in the research of organic supramolecular materials.

Triphenylene is used in optics and electronics.
Triphenylene is also used as a discotic mesogen in liquid crystalline materials.

Further, Triphenylene is a compound that fluoresces in the ultraviolet region.
In addition to this, Triphenylene is used in the preparation of triphenylene-2-carbaldehyde.

Discotic liquid crystal and organic electronics:
Triphenylene and its derivatives have been widely used in discotic liquid crystal and organic electronics as the core moiety due to its robust discotic molecular architecture.

Due to its planar structure and π-conjugated system, triphenylene has a rigid discotic structure.
This enables it to self-assemble and form highly ordered, long, cylindrical columns.

The columnar mesophases provide a direct pathway for charge carriers(electrons or holes) and avoid interruption from scattering and trapped effects in disordered materials.
This leads to efficient charge transport along the stacking direction.

Tripenylene derivatives, with flexible aliphatic side chains, can modulate intermolecular interactions.
This maintains molecular mobility under a wide temperature range and avoids excessive crystallization, and corresponding bad processability and solubility.

Triphenylene derivatives also can be synthesized through well-established routes like the Suzuki–Miyaura cross-coupling reaction.
Triphenylene's functional groups can be introduced easily and used to adjust its properties.

Recent studies synthesized new polymer structures incorporating triphenylene units and found that these materials exhibit high photoluminescence and electroluminescence efficiencies.
Their emission spectra are well-suited for blue light applications, demonstrating stability and promising performance for next-generation blue emitters.

Metal-organic frameworks and covalent organic frameworks:
Due to its delocalized system, rigid structure, stability, and adjustable structures, triphenylene can be used in the synthesis of metal–organic frameworks (MOFs) and covalent organic frameworks (COFs).
Similar to the properties mentioned in DLC applications, triphenylene and its derivatives have high conductivity, and further affect the conductivity of MOFs and COFs.
HATP-based 2D MOFs Ni3(HITP)2 single crystals can reach conductivities as high as 150 S/cm at 0K.

The rigid planar structure and three-fold symmetry of triphenylene also make it suitable for honeycomb-like 2D layered materials.
This enables supramolecular interlayer aggregation of TP-based MOFs and COFs and increases the stability and conductivity of the structure.
Triphenylene will also create uniform nanopores, which lead to high porosity and facilitate gas storage, molecular sieving, and ion exchange.

Multiple substitution sites of triphenylene bring multifunctionality to TP-base MOFs and COFs.
Depending on the different functional groups, the physical and chemical properties of frameworks can be modified easily.
In addition, due to the high chemical stability of triphenylene, Triphenylene is adaptable to various synthesis methods like solvothermal synthesis, layer-by-layer assembly, microfluidic synthesis, interfacial synthesis, etc.

Preparation of Triphenylene:
Triphenylene can be isolated from coal tar.
Triphenylene can also be synthesized in various ways.

One method is trimerization of benzyne.
This pathway first diazotizes and iodinates o-bromoaniline through HCl, NaNO2, and KI to produce o-bromoiodobenzene with a yield of 72-83%.

Then form o-bromophenyl lithium using Li and ether.
Add benzene to the organolithium intermediate to get triphenylene with a yield of 53-59%.
Impurities of biphenyl are then removed with steam distillation.

Another method involves trapping benzyne with a biphenyl derivative.
This method started with removing the trimethylsilyl group from 2-(trimethylsilyl)phenyl trifluoromethanesulfonate using cesium fluoride, generating benzyne.
Benzyne then reacts with 2-bromobiphenyl in the presence of Pd(dba)2 and tri(o-tolyl)phosphine as catalysts and produces triphenylene with a yield of 76%.

Discovery and First Synthesis of Triphenylene:
Triphenylene was first separated by German chemists H. Schmidt and Gustav Schultz [de] in 1880 from the pyrotic product of the thermal decomposition of benzene vapor.
Though triphenylene is previously referred to as chrysene, Schmidt and Schultz realized that it is an isomer of chrysene, and successfully identified and named it as triphenylene.[9]

Later in 1907, Carl Mannich first synthesized triphenylene through a two-step reaction from cyclohexanone and confirmed its planar structure.
Through predicted condensation of cyclohexanone following the pathway below, he obtained dodecahydrotriphenylene (C18H24).

Mannich then dehydrogenated dodecahydrotriphenylene into triphenylene with two methods: zinc dust distillation and copper-catalyzed dehydrogenation.
He confirmed the product was identical to the pyrolysis product from benzene by reproducing Schmidt and Schultz's experiment and comparing the samples.
Mannich also characterized triphenylene's properties, derivatives, and oxidation reactions, and confirmed it as a fully aromatic polycyclic hydrocarbon.

Stability and Reactivity of Triphenylene:

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

Reactivity:
Generally low reactivity under normal handling conditions.

Conditions to Avoid:
Excessive heat, open flames, ignition sources, and prolonged exposure to incompatible substances.

Incompatible Materials:
Strong oxidizing agents and strong acids.

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

Handling and Storage of Triphenylene:

Safe Handling:
Avoid inhaling dust and prevent contact with skin and eyes.
Use adequate ventilation and follow good industrial hygiene practices.

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

First Aid Measures of Triphenylene:

Inhalation:
Move the affected person to fresh air.
Seek medical attention if symptoms persist.

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

Eye Contact:
Rinse cautiously with plenty of water for several minutes.
Remove contact lenses if present and easy to do.

Ingestion:
Rinse mouth with water.
Obtain medical advice if discomfort develops.

Firefighting Measures of Triphenylene:

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

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

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

Accidental Release Measures of Triphenylene:

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

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

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

Exposure Controls/Personal Protective of Triphenylene:

Engineering Controls:
Provide adequate general or local exhaust ventilation.

Eye Protection:
Wear safety glasses or chemical safety goggles.

Hand Protection:
Use suitable chemical-resistant gloves.

Skin Protection:
Wear appropriate protective clothing.

Respiratory Protection:
Use a suitable particulate respirator if ventilation is insufficient or dust concentrations are elevated.

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

Identifiers of Triphenylene:
Product Name: Triphenylene
CAS No.: 217-59-4
Molecular Weight: 228.29
MDL No.: MFCD00001108
Purity/ Specification: 98%
Molecular Formula: C18H12
Storage: Sealed in dry, room temperature
SMILES Code: C12=CC=CC=C1C3=CC=CC=C3C4=CC=CC=C24

Product Number: T0513
Purity / Analysis Method : >96.0%(GC)
Molecular Formula / Molecular Weight: C18H12 = 228.29 
Physical State (20 deg.C): Solid
Storage Temperature : Room Temperature (Recommended in a cool and dark place, <15°C)
Packaging and Container : 100MG-Glass Bottle with Plastic Insert (View image),  1G-Glass Bottle with Plastic Insert (View image)
CAS RN: 217-59-4
Reaxys Registry Number: 1342908
PubChem Substance ID: 87576441
SDBS (AIST Spectral DB): 1266
Merck Index (14): 9740
MDL Number: MFCD00001108

CAS: 217-59-4
IUPAC Name: triphenylene
Molecular Formula: C18H12
InChI Key: SLGBZMMZGDRARJ-UHFFFAOYSA-N
SMILES: C1=CC=C2C(=C1)C1=CC=CC=C1C1=CC=CC=C21
Molecular Weight (g/mol): 228.29

Empirical Formula (Hill Notation): C18H12
CAS Number: 217-59-4
Molecular Weight: 228.29
UNSPSC Code: 12352100
NACRES: NA.22
PubChem Substance ID: 24900516
EC Number: 205-922-9
Beilstein/REAXYS Number: 1342908
MDL number: MFCD00001108
Assay: 98%

CAS Number: 217-59-4
ChEBI: CHEBI:33080
ChEMBL: ChEMBL1797416
ChemSpider: 8816
ECHA InfoCard: 100.005.385
EC Number: 205-922-9
KEGG: C19541
MeSH: C009590
PubChem CID: 9170
UNII: 18WX3373I0
CompTox Dashboard (EPA): DTXSID9059757
InChI: InChI=1S/C18H12/c1-2-8-14-13(7-1)15-9-3-4-11-17(15)18-12-6-5-10-16(14)18/h1-12H
Key: SLGBZMMZGDRARJ-UHFFFAOYSA-N
InChI=1/C18H12/c1-2-8-14-13(7-1)15-9-3-4-11-17(15)18-12-6-5-10-16(14)18/h1-12H
SMILES: c1(cccc3)c3c(cccc4)c4c2c1cccc2

Properties of Triphenylene:
Chemical formula: C18H12
Molar mass: 228.294 g·mol−1
Appearance: white solid
Density: 1.308 g/cm3[2]
Melting point: 198 °C; 388 °F; 471 K
Boiling point: 438 °C; 820 °F; 711 K
Magnetic susceptibility (χ): −156.6·10−6 cm3/mol

Quality Segment: 100
assay: 98%
bp: 438 °C (lit.)
mp: 195-198 °C (lit.)
fluorescence: λex 265 nm; λem 372 nm in cyclohexane
SMILES string: c1ccc2c(c1)c3ccccc3c4ccccc24
InChI: 1S/C18H12/c1-2-8-14-13(7-1)15-9-3-4-11-17(15)18-12-6-5-10-16(14)18/h1-12H
InChI key: SLGBZMMZGDRARJ-UHFFFAOYSA-N

Molecular Weight: 228.3 g/mol
XLogP3-AA: 4.9
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Rotatable Bond Count: 0
Exact Mass: 228.093900383 Da
Monoisotopic Mass: 228.093900383 Da
Topological Polar Surface Area: 0 Ų
Heavy Atom Count: 18
Complexity: 217
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

CAS No.: 217-59-4
Chemical Name: Triphenylene
CBNumber: CB0452742
Molecular Formula: C18H12
Molecular Weight: 228.29
MDL Number: MFCD00001108

Melting point: 195-198 °C(lit.)
Boiling point: 438 °C(lit.)
Density: 1.302
refractive index: 1.5500 (estimate)
Flash point: 438°C
storage temp.: Sealed in dry,Room Temperature
solubility: Soluble in ethanol, benzene, acetic acid, oils and chloroform.
form: Crystalline Needles
color: White to beige
Water Solubility: 6.6ug/L(25.00 ºC)
λmax: 335nm(Hexane)(lit.)
Merck: 14,9740
BRN: 1342908
Henry's Law Constant: 6.4×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Major Application: environmental
InChI: 1S/C18H12/c1-2-8-14-13(7-1)15-9-3-4-11-17(15)18-12-6-5-10-16(14)18/h1-12H
InChIKey: SLGBZMMZGDRARJ-UHFFFAOYSA-N
SMILES: c1ccc2c(c1)c3ccccc3c4ccccc24
CAS DataBase Reference: 217-59-4(CAS DataBase Reference)
EWG's Food Scores: 1
FDA UNII: 18WX3373I0
NIST Chemistry Reference: Triphenylene(217-59-4)
IARC: 3 (Vol. Sup 7, 92) 2010
EPA Substance Registry System: Triphenylene (217-59-4)
UNSPSC Code: 41116107
NACRES: NA.24

Specifications of Triphenylene:
Appearance: White to Light yellow to Dark green powder to crystal
Purity(GC): min. 96.0 %
Melting point: 196.0 to 200.0 °C
NMR: confirm to structure

Assay (HPLC): ≥97.5%
Form: Crystals or powder or crystalline powder or granules
Appearance (Color): White to cream to yellow to pale brown

Related Compounds of Triphenylene:
Benzene
Coronene
Phenanthrene
Diphenylene
Tetraphenylene
Trinaphthylene
Triptycene
ortho-Terphenyl

Related tetracyclic PAHs: 
Pyrene
Chrysene
Benz(a)anthracene
Benzo(c)phenanthrene
Tricyclobutabenzene

Names of Triphenylene:

Preferred IUPAC name:
Triphenylene

Other names:
Benzo[l]phenanthrene
9,10-Benzophenanthrene
1,2,3,4-Dibenzonaphthalene
Isochrysene