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.
|Molecular weight||366.01 g/mol|
|HOMO/LUMO||HOMO = 6.99 eV, LUMO = 4.44 eV|
|Classification / Family||Phenanthrene, semiconductor synthesis intermediates, low band gap polymers, OLED, OFETs, organic photovoltaics|
|Purity||>97% (1H NMR in CDCl3)|
|Melting point||Tm = 274.3 °C|
|Appearance||Orange to red powder/crystals|
Literature and Reviews
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.
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.
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.
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.
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.
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.
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.
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.
- 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.
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