9,10-Diphenylanthracene

Chemical Properties

9,10-Diphenylanthracene is a fluorescent compound, slightly yellow powder with an excitation peak at 314 nm and an emission peak at 302 nm. It is spectrally similar to MCA (7-Methoxycoumarin-4-acetic acid). 

Uses

9,10-Diphenylanthracene acts as a sensitizer in chemiluminescence. It is used in light sticks in order to produce blue light. It is also useful in blue organic light-emitting diodes (OLEDs) and OLED-based displays. Further, it plays an important role in the preparation of 9,10-difluoro-9,10-diphenyl-9,10-dihydro-anthracene. In addition to this, it is used as an organic semiconductor.

Definition

ChEBI: 9,10-diphenylanthracene is a member of the class of anthracenes that is anthracene in which both of the hydrogens on the central ring are substituted by phenyl groups. It has a role as a fluorochrome and a photosensitizing agent.

Application

9,10-Diphenylanthracene is a polycyclic aromatic hydrocarbon and a useful organic semiconductor. 9,10-Diphenylanthracene is also a sensitiser in chemiluminescence. It has applications related to OLEDs and OLED-based displays.

General Description

9,10-Diphenylanthracene, an aromatic hydrocarbon, is a blue light emitting material that is used for the measurement of fluorescence quantum yields in dilute solutions. Its derivatives show potential candidature in organic light emitting diode (OLED) devices. It is also used as a fluorophore for the study of peroxyoxalate chemiluminescence (POCL).

Synthesis

9, 10 – Diphenylanthracene was synthesized via a multistep synthesis using 9, 10 – dibromoanthracene, a Suzuki coupling was performed using phenylboronic acid over a tetrakis(triphenylphosphine)palladium(0) catalyst to form the title compound:
The mixture of 1,3-dibromobenzene (236 mg, 1.0 mmol), phenylboronic acid (271 mg, 2.2 mmol), and Na2CO3 (424 mg, 4 mmol) was taken up in DMF (2 mL) and then ARF-Pd (300 mg, 0.01 mmol Pd) was added. The mixture was heated under N2 at 110 °C for 2.5 h. After cooling, the mixture was diluted with cold H2O (10 mL) and filtered through a cotton bed. The filtrate was extracted with Et2O (3 × 20 mL) and the combined organic extracts were washed with brine (10 mL), dried (Na2SO4), and evaporated. The residue was purified by column chromatography (silica gel, PE) to give 9,10-Diphenylanthracene (4d), yield 90%. Mp 245-247 °C (Lit.36 245-48 °C). IR (Nujol): 1458, 1377 cm-1. 1H NMR (300 MHz, CDCl3): δ = 7.72-7.66 (m, 4 H), 7.62-7.46 (m, 10 H), 7.34-7.29 (m, 4 H). 13C NMR (75 MHz, CDCl3): δ = 139.1, 137.1, 131.3, 129.8, 128.4, 127.4, 126.9, 125.0.

Purification Methods

Crystallise the anthracene from acetic acid or xylene [Baumstark et al. J Org Chem 52 3308 1987]. [Beilstein 5 IV 2807.]