Skip to main content

Triphenylene

ADVERTISEMENT
Identification
Molecular formula
C18H12
CAS number
217-59-4
IUPAC name
triphenylene
State
State
Triphenylene is typically solid at room temperature, forming white crystals.
Melting point (Celsius)
198.00
Melting point (Kelvin)
471.15
Boiling point (Celsius)
438.00
Boiling point (Kelvin)
711.15
General information
Molecular weight
228.29g/mol
Molar mass
228.2870g/mol
Density
1.2800g/cm3
Appearence
Triphenylene is a polycyclic aromatic hydrocarbon, which appears as a white crystalline solid.
Comment on solubility

Solubility of Triphenylene

Triphenylene (C18H12) is an interesting polycyclic aromatic hydrocarbon known for its unique molecular structure and properties. When it comes to solubility, there are several key points worth noting:

  • Solvent Types: Triphenylene is notably insoluble in water, which is a characteristic behavior of many aromatic compounds due to their nonpolar nature.
  • Organic Solvents: However, it readily dissolves in nonpolar organic solvents such as benzene, toluene, and chloroform. This solubility in organic media is attributed to similar intermolecular forces.
  • Concentration Effect: The degree of solubility can vary significantly; at room temperature, triphenylene can dissolve in generous amounts in suitable organic solvents.
  • Temperature Influence: Increasing the temperature typically enhances the solubility of triphenylene in nonpolar solvents due to increased kinetic energy, which helps to overcome lattice energy.

In conclusion, while triphenylene demonstrates strong solubility properties in nonpolar solvents, its lack of solubility in polar solvents like water highlights the critical role of molecular structure in dictating solubility behavior. Understanding these interactions is essential for applications in materials science and organic chemistry.

Interesting facts

Interesting Facts about Triphenylene

Triphenylene is an aromatic hydrocarbon that serves as a fascinating subject in organic chemistry due to its unique structural and electronic properties.

Structure and Characteristics

Triphenylene consists of four fused benzene rings, creating a flat, planar structure. This configuration leads to a high degree of symmetry and stability, making it an important compound in various applications.

Applications

  • Organic Electronics: Due to its excellent electron-accepting properties, triphenylene is commonly used in organic semiconductors, such as organic light-emitting diodes (OLEDs) and organic photovoltaic cells.
  • Fluorescent Dyes: Its photoactive nature makes triphenylene a popular choice for fluorescent probes and dyes in research and imaging applications.
  • Polymer Chemistry: Triphenylene is utilized in the synthesis of various polymers and materials, improving adaptability and functionality.

Chemical Behavior

Because of its aromatic structure, triphenylene exhibits significant stability and resistance to chemical reaction. However, it can undergo reactions such as:

  • Electrophilic Substitution: Its electrons can participate in electrophilic aromatic substitution reactions.
  • Photochemical Reactions: Exposure to ultraviolet light can induce various photochemical transformations.

Environmental Impact

While triphenylene finds valuable applications, it is essential to acknowledge its environmental impact. As with many organic compounds, understanding its behavior in biological systems is crucial for assessing toxicity and ecological effects.

Fun Fact

Did you know that triphenylene is named after its chemical structure? The name reflects its composition of three "phenylene" units; the prefix "tri" signifies the three distinct phenyl groups joined together!

In summary, triphenylene is not only a compound of theoretical significance but also boasts vast practical implications across various fields, making it a noteworthy compound in the realm of chemistry.

Synonyms
TRIPHENYLENE
217-59-4
9,10-Benzophenanthrene
Isochrysene
Benzo[l]phenanthrene
9,10-Benzphenanthrene
Benzo(l)phenanthrene
1,2,3,4-Dibenznaphthalene
CCRIS 1301
CHEBI:33080
EINECS 205-922-9
MFCD00001108
NSC 57455
NSC-57455
TRIPHENYLENE [MI]
18WX3373I0
TRIPHENYLENE [IARC]
DTXSID9059757
UNII-18WX3373I0
TRIPHENYLENE (IARC)
1,2:3,4-Dibenznaphthalene
triphenylen
Triphenylene, 97%
Triphenylene, 98%
9,10Benzphenanthrene
9,10benzophenanthrene
Triphenylene 10 microg/mL in Cyclohexane
Triphenylene 10 microg/mL in Acetonitrile
1,3,4-Dibenznaphthalene
1,2,3,4Dibenznaphthalene
CHEMBL1797416
DTXCID7036537
Triphenylene, analytical standard
ALBB-035099
NSC57455
BBL100122
CX1148
STK368374
AKOS004908298
Triphenylene (purified by sublimation)
CS-W018431
FT33664
SB66862
AS-19089
SY019503
NS00026961
T0513
T3267
C19541
Triphenylene, BCR(R) certified Reference Material
Q2975866
205-922-9
53814-75-8