2,7-Dibromophenanthrene-9,10-dione (CAS 84405-44-7), also known as 27PNDO, is a phenanthrenedione intermediate for building semiconducting small molecules, oligomers and polymers. It is supplied by Ossila at >97% purity (1H NMR in CDCl3) as an orange to red powder or crystals.
Structurally, the compound is an isomer of 2,6-dibromoanthraquinone and can be viewed as 4,4'-dibromobiphenyl linked by a 1,2-diketone bridge. The bromine atoms at the 2 and 7 positions allow C-C coupling reactions that extend the conjugated core, while the diketone unit condenses with diamines to give quinoxalines.
In reported work, purely organic phosphorescent light-emitting diodes using this compound as the emitter with a 6,11-dibromodibenzo[f,h]quinoxaline host gave an external quantum efficiency of 0.11%. An OLED built on DQBC, which has a dibenzo[a,c]phenazine core, reached a maximum external quantum efficiency of 39.1% and a maximum power efficiency of 112.0 lm W-1 without external light-extraction techniques.
- Synthesis of semiconducting small molecules, oligomers and polymers for organic field-effect transistors (OFETs).
- Preparation of emitter and host materials for organic light-emitting diodes (OLEDs).
- Building block for organic photovoltaic (OPV) and low band gap polymer materials.
- Monomer for the synthesis of covalent organic frameworks (COFs).
- Formation of quinoxaline derivatives by condensation with diamines.
| Brand | Ossila |
|---|---|
| CAS number | 84405-44-7 |
| Molecular formula | C14H6Br2O2 |
| Purity | >97% (1H NMR in CDCl3) |
| Category | — |
| Pack sizes | 5 g, 10 g, 25 g, 50 g |
| Physical form | Orange to red powder/crystals |
| Storage | — |
- Product code: B1031
- Molecular Weight: 366.01 g/mol
- Synonyms: 2,7-Dibromo-9,10-phenanthrenedione, 27PNDO
- HOMO/LUMO: HOMO = 6.99 eV, LUMO = 4.44 eV
- Melting Point: Tm = 274.3 °C
—
—