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2,7-Dibromophenanthrene-9,10-dione


Product Code B1031-5g
Price $171.00 ex. VAT

2,7-Dibromophenanthrene-9,10-dione

Very useful intermediate for the synthesis of semiconducting small molecule, oligomers and polymers in applications of OFETs, OLEDs and OPVs.


2,7-Dibromophenanthrene-9,10-dione, one of the isomers of 2,6-dibromoanthraquinone, can be considered as a 4,4'-dibromobiphenyl bridged by 1,2-diketones. Bromo-function groups at 2,7-postions gives rise to further C-C formation reactions to extend conjugation to its core structure while diketone can form quinoxalines via condensation with diamines. 2,7-Dibromophenanthrene-9,10-dione is very useful intermediate for the synthesis of semiconducting small molecule, oligomers and polymers in applications of OFETs, OLEDs and OPVs.

Pure organic based phosphorescent light-emitting diodes based on 2,7-dibromophenanthrene-9,10-dione as an emitter and bromine modified 6,11-dibromodibenzo[f,h]quinoxaline as a host showed phosphorescent emission with an external quantum efficiency of 0.11%. OLED device based on DQBC with a dibenzo[a,c]phenazine core achieves maximum external quantum efficiency of 39.1% without any external light-extraction techniques, together with a maximum power efficiency of 112.0 lm W-1 and alleviated efficiency roll-off.

General Information

CAS number 84405-44-7
Chemical formula C14H6Br2O2
Full name 2,7-Dibromophenanthrene-9,10-dione
Molecular weight 366.01 g/mol
Synonyms 2,7-Dibromo-9,10-phenanthrenedione, 27PNDO
HOMO/LUMO HOMO = 6.99 eV, LUMO = 4.44 eV
Classification / Family Phenanthrene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics

Chemical Structure

2,7-Dibromophenanthrene-9,10-dione chemical structure
2,7-Dibromophenanthrene-9,10-dione (27PNDO) chemical structure, CAS 84405-44-7

Product Details

Purity >97% (1H NMR in CDCl3)
Melting point T= 274.3 °C
Appearance Orange to red powder/crystals

MSDS Documentation

2,7-Dibromophenanthrene-9,10-dione2,7-Dibromophenanthrene-9,10-dione MSDS Sheet

Literature and Reviews

  1. T and V-shaped donor-acceptor fluorophores involving pyridoquinoxaline: large Stokes shift, environment-sensitive tunable emission and temperature-induced fluorochromism, B. Sk et al., Chem. Commun., 54, 1786-1789 (2018); DOI: 10.1039/C7CC09261J.
  2. Structure-property relationship of D-A type copolymers based on phenanthrene and naphthalene units for organic electronics, Y. Kim et al., J. Mater. Chem. C, 5, 10332-10342 (2017); DOI: 10.1039/C7TC02925J.
  3. The Extension of Conjugated System in Pyridyl-Substituted Monoazatriphenylenes for the Tuning of Photophysical Properties, D. Kopchuk et al., Chem. Heterocycl. Comp. 50, 871–879 (2014); DOI: 10.1007/s10593-014-1541-0.
  4. Synthesis of electron-accepting polymers containing phenanthra-9,10-quinone units, J. Gautrot et al., J. Mater. Chem., 19, 4148-4156 (2009); DOI: 10.1039/B901853K.
  5. Metal-free and purely organic phosphorescent light-emitting diodes using phosphorescence harvesting hosts and organic phosphorescent emitters, D. Lee et al., J. Mater. Chem. C, 7, 11500-11506 (2019); DOI: 10.1039/C9TC03203G.
  6. Color tuning of dibenzo[a,c]phenazine-2,7-dicarbonitrile-derived thermally activated delayed fluorescence emitters from yellow to deep-red, S. Kothavale et al., J. Mater. Chem. C, 8, 7059-7066 (2020); DOI: 10.1039/d0tc00960a.
  7. The effect of the donor unit on the optical properties of polymers, E. Unve et al., Org. Electron., 12 (10), 1625-1631 (2011); DOI: 10.1016/j.orgel.2011.06.004.
  8. Approaching Nearly 40% External Quantum Efficiency in Organic Light Emitting Diodes Utilizing a Green Thermally Activated Delayed Fluorescence Emitter with an Extended Linear Donor–Acceptor–Donor Structure, Y. Chen et al., Adv. Mater., 33 (44), 2103293 (2021); DOI: 10.1002/adma.202103293.
  9. Highly efficient red thermally activated delayed fluorescence materials based on a cyano-containing planar acceptor, J. Mater. Chem. C, 7, 15301-15307 (2019); DOI: 10.1039/C9TC05349B.

To the best of our knowledge the information provided here is accurate. However, Ossila assume no liability for the accuracy of this page. The values provided are typical at the time of manufacture and may vary over time and from batch to batch. All products are for laboratory and research and development use only, and may not be used for any other purpose including health care, pharmaceuticals, cosmetics, food or commercial applications.

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