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Triphenylene

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Triphenylene Basic information

Product Name:
Triphenylene
Synonyms:
  • BENZO(L)PHENANTHRENE
  • ISOCHRYSENE
  • 9,10-BENZOPHENANTHRENE
  • 1,2:3,4-DIBENZNAPHTHALENE
  • TRIPHENYLENE
  • 9,10-Benzphenanthrene
  • benzo(1)phenanthrene
  • Triphenylene,98%
CAS:
217-59-4
MF:
C18H12
MW:
228.29
EINECS:
205-922-9
Product Categories:
  • Aromatic Hydrocarbons (substituted) & Derivatives
  • Naphthyridine,Quinoline
  • OLED materials,pharm chemical,electronic
Mol File:
217-59-4.mol
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Triphenylene Chemical Properties

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
InChIKey
SLGBZMMZGDRARJ-UHFFFAOYSA-N
CAS DataBase Reference
217-59-4(CAS DataBase Reference)
NIST Chemistry Reference
Triphenylene(217-59-4)
IARC
3 (Vol. Sup 7, 92) 2010
EPA Substance Registry System
Triphenylene (217-59-4)
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Safety Information

Hazard Codes 
Xi,N
Risk Statements 
41-50/53
Safety Statements 
22-24/25-61-60-39-26
RIDADR 
UN 3077 9/PG 3
WGK Germany 
3
RTECS 
YK2925000
HazardClass 
9
PackingGroup 
HS Code 
29029090

MSDS

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Triphenylene Usage And Synthesis

Chemical Properties

white to beige crystalline needles

Uses

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.

Definition

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

Application

Triphenylene is an important basic skeleton monomer of polycyclic aromatic hydrocarbons. It 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. It is also used as a discotic mesogen in liquid crystalline materials. Further, it is a compound that fluoresces in the ultraviolet region. In addition to this, it is used in the preparation of triphenylene-2-carbaldehyde.

Preparation

Triphenylene synthesis: 2-Chlorobenzoic acid(78mg, 0.5mmol), iodonium salt (236mg, 0.55mmol), palladium acetate (2.8mg, 0.0125mmol), potassium carbonate (152mg, 1.1mmol) were dissolved in 3mL of NMP solvent was heated to 110 °C and stirred for 17 hours, cooled to room temperature, extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, concentrated, and subjected to column chromatography to obtain 92 mg of triphenylene as a white solid, The yield was 80%.

Synthesis Reference(s)

Synthesis, p. 756, 1992 DOI: 10.1055/s-1992-26218

General Description

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.

Purification Methods

Purify triphenylene by zone refining or crystallisation from EtOH or CHCl3 and sublime. [Beilstein 5 IV 2556.]

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