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%.
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.
Synthesis
Triphenylene can be synthesized by a novel ligand-free Pd-catalyzed cascade reaction between o-chlorobenzoic acids and cyclic diaryliodonium salts.
[1]
Purification Methods
Purify triphenylene by zone refining or crystallisation from EtOH or CHCl3 and sublime. [Beilstein 5 IV 2556.]
References
[1] Shuai Yang.“Synthesis of Functionalized Triphenylenes via a Traceless Directing Group Strategy.” Organic Letters 20 6 (2018): 1491–1495.
