| Identification | Back Directory | [Name]
9,9-diphenyl-9,10-dihydroacridine | [CAS]
20474-15-1 | [Synonyms]
9,9-Diphenylacridan
9,9-Diphenyl-10H-acridine
9,10-dihydro-9,9-diphenylacridin
9,10-Dihydro-9,9-diphenylacridine
9,9-diphenyl-9,10-dihydroacridine
Acridine, 9,10-dihydro-9,9-diphenyl- | [Molecular Formula]
C25H19N | [MDL Number]
MFCD28127357 | [MOL File]
20474-15-1.mol | [Molecular Weight]
333.425 |
| Chemical Properties | Back Directory | [Melting point ]
249.0 to 254.0 °C | [Boiling point ]
463.9±45.0 °C(Predicted) | [density ]
1.154±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
powder to crystal | [pka]
1.15±0.40(Predicted) | [color ]
White to Orange to Green | [λmax]
320nm(CH3CN)(lit.) | [InChI]
InChI=1S/C25H19N/c1-3-11-19(12-4-1)25(20-13-5-2-6-14-20)21-15-7-9-17-23(21)26-24-18-10-8-16-22(24)25/h1-18,26H | [InChIKey]
HWTHOPMRUCFPBX-UHFFFAOYSA-N | [SMILES]
C1=C2C(NC3=C(C2(C2=CC=CC=C2)C2=CC=CC=C2)C=CC=C3)=CC=C1 | [CAS DataBase Reference]
20474-15-1 |
| Questions and Answers (Q&A) | Back Directory | [Description]
9,9-diphenyl-9,10-dihydroacridine is a dihydrouridine derivatives. It has several applications. It is ausefulraw materials of OLEDs, leading to OLEDs with excellent blue-light emission property, suitable energy levels, high mobility as well as good thermal stability. It can also be supplemented to platinum complexes, making it suitable for use as phosphorescent emitters or as delayed fluorescent and phosphorescent emitters.
| [References]
Reddy, Saripally Sudhaker, et al. "Multi-functional highly efficient bipolar 9,9-dimethyl-9,10-dihydroacridine/imidazole-based materials for solution-processed organic light-emitting diode applications." Dyes & Pigments 134(2016):315-324.
Li, Jian. "Tetradentate cyclometalated platinum complexes containing 9,10-dihydroacridine and its analogues." (2015).
|
| Hazard Information | Back Directory | [Uses]
9,9-Diphenyl-9,10-dihydroacridine is a reagent used in the synthesis and in the studies of acridan derivatives as antioxidants. | [Synthesis]
General procedure for the synthesis of 9,9-diphenyl-9,10-dihydroacridine from benzophenone and (2-bromophenyl)aniline: firstly, 10 g of (2-bromophenyl)aniline was dissolved in 100 mL of tetrahydrofuran, and the reaction system was subsequently cooled to -78 °C. At this temperature, 20 mL of 2.5 M butyl lithium solution was slowly added and stirred continuously for 1 hour. Next, 11 g of benzophenone was dissolved in 100 mL of tetrahydrofuran and slowly added dropwise to the reaction system. After the dropwise addition, the reaction temperature was gradually increased to room temperature and stirring was continued for 12 hours. Upon completion of the reaction, extraction was carried out with distilled water and dichloromethane, and the organic phase was dried with anhydrous magnesium sulfate, followed by filtration under reduced pressure to obtain the crude product. The crude product was dissolved in 100 mL of acetic acid, and 7 mL of concentrated sulfuric acid was added slowly and dropwise, and then the mixture was heated and refluxed and stirred. At the end of the reaction, it was again extracted with distilled water and dichloromethane. Finally, the resulting solid was purified by column chromatography to afford intermediate B-1 (7.1 g, 53% yield). |
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