868850-50-4

Basic information

• Product Name: 2,6-bis(diphenylaMino)anthracene-9,10-dione
• Synonyms: 2,6-bis(diphenylaMino)anthracene-9,10-dione;2,6-bis(diphenylamino)-9,10-Anthracenedione;2,6-Bis(diphenylamino)anthraquinone;2,6-bis(N-phenylanilino)anthracene-9,10-dione
• CAS NO: 868850-50-4
• Molecular Formula: C₃₈H₂₆N₂O₂
• Molecular Weight: 542.62524
• EINECS: -0
• Mol File: 868850-50-4.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,6-bis(diphenylaMino)anthracene-9,10-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-bis(diphenylaMino)anthracene-9,10-dione(868850-50-4)
• EPA Substance Registry System: 2,6-bis(diphenylaMino)anthracene-9,10-dione(868850-50-4)

Safety Data

• Hazardous Substances Data: 868850-50-4(Hazardous Substances Data)

Usage

Uses

2,6-Bis(diphenylamino)anthraquinone (CAS# 868850-50-4) is a useful organic charge transfer compound and dye, whose charge transfer-induced torsional dynamics have been documented.

Upstream product

• 633-70-5 2,6-dibromoanthraquinone 
• 122-39-4 diphenylamine 
• 605-40-3 2,6-dichloro-9,10-anthraquinone 

Downstream Products

• 926033-10-5 2,6-bis(diphenylamino)-9,10-[di-(2-naphthyl)]-9,10-dihydro-9,10-anthracenediol 

Relevant articles and documents

Anthraquinone-based intramolecular charge-transfer compounds: Computational molecular design, thermally activated delayed fluorescence, and highly efficient red electroluminescence

Red fluorescent molecules suffer from large, non-radiative internal conversion rates (kIC) governed by the energy gap law. To design efficient red thermally activated delayed fluorescence (TADF) emitters for organic light-emitting diodes (OLEDs), a large fluorescence rate (kF) as well as a small energy difference between the lowest singlet and triplet excited states (ΔEST) is necessary. Herein, we demonstrated that increasing the distance between donor (D) and acceptor (A) in intramolecular-charge-transfer molecules is a promising strategy for simultaneously achieving small ΔEST and large kF. Four D-Ph-A-Ph-D-type molecules with an anthraquinone acceptor, phenyl (Ph) bridge, and various donors were designed, synthesized, and compared with corresponding D-A-D-type molecules. Yellow to red TADF was observed from all of them. The kF and ΔEST values determined from the measurements of quantum yield and lifetime of the fluorescence and TADF components are in good agreement with those predicted by corrected time-dependent density functional theory and are approximatively proportional to the square of the cosine of the theoretical twisting angles between each subunit. However, the introduction of a Ph-bridge was found to enhance kF without increasing ΔEST. Molecular simulation revealed a twisting and stretching motion of the N-C bond in the D-A-type molecules, which is thought to lower ΔEST and kF but raise kIC, that was experimentally confirmed in both solution and doped film. OLEDs containing D-Ph-A-Ph-D-type molecules with diphenylamine and bis(4-biphenyl)amine donors demonstrated maximum external quantum efficiencies of 12.5% and 9.0% with emission peaks at 624 and 637 nm, respectively.