32497-38-4

Basic information

• Product Name: N,N'-(9,9',10,10'-tetrahydro-9,9',10',10'-tetraoxo[1,1'-bianthracene]-2,2'-diyl)bisacetamide
• Synonyms: N,N'-(9,9',10,10'-tetrahydro-9,9',10',10'-tetraoxo[1,1'-bianthracene]-2,2'-diyl)bisacetamide
• CAS NO: 32497-38-4
• Molecular Formula: C₃₂H₂₀N₂O₆
• Molecular Weight: 478.49538
• EINECS: 251-066-4
• Mol File: 32497-38-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 870.2°Cat760mmHg
• Flash Point: 269.5°C
• Appearance: /
• Density: 1.467g/cm³
• CAS DataBase Reference: N,N'-(9,9',10,10'-tetrahydro-9,9',10',10'-tetraoxo[1,1'-bianthracene]-2,2'-diyl)bisacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-(9,9',10,10'-tetrahydro-9,9',10',10'-tetraoxo[1,1'-bianthracene]-2,2'-diyl)bisacetamide(32497-38-4)
• EPA Substance Registry System: N,N'-(9,9',10,10'-tetrahydro-9,9',10',10'-tetraoxo[1,1'-bianthracene]-2,2'-diyl)bisacetamide(32497-38-4)

Safety Data

• Hazardous Substances Data: 32497-38-4(Hazardous Substances Data)

Upstream product

• 117-79-3 2-aminoanthraquinone 

Downstream Products

• 475-71-8 flavanthrone 

Relevant articles and documents

Soluble Flavanthrone Derivatives: Synthesis, Characterization, and Application to Organic Light-Emitting Diodes

Simple modification of benzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridine-8,16-dione, an old and almost-forgotten vat dye, by reduction of its carbonyl groups and subsequent O-alkylation, yields solution-processable, electroactive, conjugated compounds of the periazaacene type, suitable for the use in organic electronics. Their electrochemically determined ionization potential and electron affinity of about 5.2 and -3.2 eV, respectively, are essentially independent of the length of the alkoxyl substituent and in good agreement with DFT calculations. The crystal structure of 8,16-dioctyloxybenzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridine (FC-8), the most promising compound, was solved. It crystallizes in space group P1 and forms π-stacked columns held together in the 3D structure by dispersion forces, mainly between interdigitated alkyl chains. Molecules of FC-8 have a strong tendency to self-organize in monolayers deposited on a highly oriented pyrolytic graphite surface, as observed by STM. 8,16-Dialkoxybenzo[h]benz[5,6]acridino[2,1,9,8-klmna]acridines are highly luminescent, and all have photoluminescence quantum yields of about 80 %. They show efficient electroluminescence, and can be used as guest molecules with a 4,4′-bis(N-carbazolyl)-1,1′-biphenyl host in guest/host-type organic light-emitting diodes. The best fabricated diodes showed a luminance of about 1900 cd m-12, a luminance efficiency of about 3 cd A-1, and external quantum efficiencies exceeding 0.9 %. New life for an old dye: Simple modification of flavanthrone, an old, intractable, and almost-forgotten vat dye, by reduction of its carbonyl groups to phenolates followed by O-alkylation, gave a new group of solution-processable, electroactive, conjugated compounds (see figure). Their HOMO and LUMO energies, as well as their ionization potentials and electron affinities, make them suitable for application as components of organic light-emitting diodes.