84405-44-7

Basic information

• Product Name: 2,7-Dibromo-9,10-phenanthrenedione
• Synonyms: 2,7-DIBROMO-9,10-PHENANTHRENEDIONE;2,7-dibromo-phenanthrene-9,10-dione;2,7-Dibromo-9,10-phenanthrenequinone;2,7-dibroMo-9,10-dihydrophenanthrene-9,10-dione;1g/2100;2,7-DibroMo-9,10-Dihydrophenanthrene-9,10-Dione,2,7-Dibromo-9,10-Phenanthrenequinone;2,7-Dibromo-9,10-phenanthren
• CAS NO: 84405-44-7
• Molecular Formula: C₁₄H₆Br₂O₂
• Molecular Weight: 366
• EINECS: 1592732-453-0
• Product Categories: Electronic Chemicals;Naphthyridine,Quinoline
• Mol File: 84405-44-7.mol
• Article Data: 32

Chemical Properties

• Melting Point: 331°C(lit.)
• Boiling Point: 503.8 °C at 760 mmHg
• Flash Point: 179.1 °C
• Appearance: yellow powder
• Density: 1.911 g/cm₃
• Vapor Pressure: 2.81E-10mmHg at 25°C
• Refractive Index: 1.7
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2,7-Dibromo-9,10-phenanthrenedione(CAS DataBase Reference)
• NIST Chemistry Reference: 2,7-Dibromo-9,10-phenanthrenedione(84405-44-7)
• EPA Substance Registry System: 2,7-Dibromo-9,10-phenanthrenedione(84405-44-7)

Safety Data

• Hazardous Substances Data: 84405-44-7(Hazardous Substances Data)

Usage

Chemical Properties

light yellow solid

Uses

2,7-Dibromophenanthrene-9,10-dione is used as a modifier in solar cells.

InChI:InChI=1/C14H6Br2O2/c15-7-1-3-9-10-4-2-8(16)6-12(10)14(18)13(17)11(9)5-7/h1-6H

Upstream product

• 7732-18-5 water 
• 7726-95-6 bromine 
• 84-11-7 9,10-phenanthrenequinone 
• 7647-01-0 hydrogenchloride 
• 98-71-5 4-hydrazino-benzenesulfonic acid 
• 53622-33-6 2-bromo-phenanthrene-9,10-dione 
• 85-01-8 phenanthrene 
• 61650-86-0 C₁₄H₉Br₂N 
• 62325-30-8 2,7-dibromophenanthrene 
• 64-19-7 acetic acid 

Downstream Products

• 54389-67-2 4,4‘-dibromo-2,2‘-bis(carboxyl)-1,1‘-biphenyl 
• 1174669-47-6 2,7-bis(9',9'-dioctylfluoren-2'-yl)-9,10-phenanthraquinone 

Relevant articles and documents

Photoresponsive porous materials: The design and synthesis of photochromic diarylethene-based linkers and a metal-organic framework

The synthesis and characterization of novel photochromic diarylethene-based linkers for use in metal-organic frameworks is described including crystal structure analysis of nearly all reaction intermediates. The bis-carboxylated dithien-3-ylphenanthrenes can be prepared under relatively mild conditions in high yield and were subsequently used to create a photoresponsive metal-organic framework, UBMOF-1. While the photochromism of the ligand TPDC in solution is fully reversible, the cycloreversion reaction is suppressed when this linker is incorporated into the crystalline framework of UBMOF-1. The Royal Society of Chemistry 2014.

Effect of side chains on phenanthrene based D-A type copolymers for polymer solar cells

A series of low band gap conjugated copolymers containing 9,10-modified phenanthrene and diketopyrrolopyrrole (DPP) units were synthesized as electron donor materials for bulk heterojunction organic solar cells. These donor-acceptor type PDPP copolymers have varying solubilizing groups on their identical conjugated backbones. The optical bandgap of PDPP copolymers is about 1.6?eV which corresponds to the long wavelength region of the solar spectrum. Through the incorporation of phenanthrene units into the conjugated backbone instead of commonly used thiophene derivatives, a higher open-circuit voltage of about 0.8?V could be achieved, as a result of their deeper HOMO level. Of all the devices, the P4:PC61BM BHJ system showed the best performance with a Voc of 0.79?V, a Jsc of 5.97?mA?cm?2, a fill factor of 0.62 and a power conversion efficiency of 2.73% due to superior nanoscale phase separation between the electron donor and electron acceptor materials than in the other polymers arising from short-branched solubilizing groups on the phenanthrene side of its conjugated backbone.

Synthesis of Redox-Active Photochromic Phenanthrene Derivatives

A phenanthrene unit has been functionalized by several methylthiophene units in order to bring it a photochromic behavior. These compounds were characterized by NMR, absorption and emission spectroscopies, theoretical calculations as well as cyclic voltammetry. The association of a phenanthrene group with a photochromic center could open the door to a new generation of organic field-effect transistors.

Tunable Redox Potential Photocatalyst: Aggregates of 2,3-Dicyanopyrazino Phenanthrene Derivatives for the Visible-Light-Induced α-Allylation of Amines

This work highlights the tunable redox potential of 6,11-dibromo-2,3-dicyanopyrazinophenanthrene (DCPP3) aggregates, which can be formed through physical π-πstacking interactions with other DCPP3 monomers. Electrochemical and scanning electron microscopy showed that the reduction potential of [DCPP3]n aggregates could be increased by decreasing their size. The size of [DCPP3]n aggregates could be regulated by controlling the concentration of DCPP3 in an organic solvent. As such, a fundamental understanding of this tunable redox potential is essential for developing new materials for photocatalytic applications. The [DCPP3]n aggregates as a visible-light photocatalyst in combination with Pd catalysts in the visible-light-induced α-allylation of amines were used. This [DCPP3]n photocatalyst exhibits excellent photo- and electrochemical properties, including a remarkable visible-light absorption, long excited-state lifetime (16.6 μs), good triplet quantum yield (0.538), and high reduction potential (Ered([DCPP3]n/[DCPP3]n-) > -1.8 V vs SCE).

UV to NIR multistate electrochromism and electrofluorochromism in dibenzophenazine-arylamine derivatives

An intriguing case of intramolecular and intervalence charge transfer-driven multistate electrochromism and electrofluorochromism in dibenzophenazin-(phenyl)methanone and arylamine-based redox-active donor-acceptor-donor molecules was elucidated. Tunable