84405-44-7

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

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

Downstream Products

• 54389-67-2 4,4‘-dibromo-2,2‘-bis(carboxyl)-1,1‘-biphenyl 
• 14348-75-5 2,7-dibromofluorene-9-one 
• 502486-13-7 2,7-dibromo-9-hydroxy-fluorene-9-carboxylic acid 
• 1004539-50-7 5,10-dibromo-1,3-diphenyl-2H-cyclopenta-[l]phenanthren-2-one 
• 1004539-59-6 C₄₅H₄₈Br₂O₃ 
• 1010812-08-4 2,7-dibromo-9,10-di(p-tolyl)-9,10-dihydro-phenanthrene-9,10-diol 
• 1010812-07-3 2,7-dibromo-9,10-di(4-dodecylphenyl)-9,10-dihydro-phenanthrene-9,10-diol 
• 1174669-47-6 2,7-bis(9',9'-dioctylfluoren-2'-yl)-9,10-phenanthraquinone 
• 1371570-92-1 5,10-dibromo-2,3-diphenyl-2,3-dihydrophenanthro[9,10-b]furan 
• 1371570-17-0 C₅₂H₃₆N₂O 
• 1371570-24-9 C₅₂H₃₂N₂O 
• 1371570-96-5 C₄₀H₄₀B₂O₅ 
• 1371570-93-2 5,10-dibromo-benzo-phenanthro[9,10b]-furan 
• 1375171-45-1 5,10-dibromo-2-(4-((2-ethylhexyl)oxy)phenyl)-1-hexyl-1H-phenanthro[9,10-d]imidazole 

Relevant academic research and scientific papers

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.

Redox Mechanisms in Li and Mg Batteries Containing Poly(phenanthrene quinone)/Graphene Cathodes using Operando ATR-IR Spectroscopy

The redox reaction mechanism of a poly(phenanthrene quinone)/graphene composite (PFQ/rGO) was investigated using operando attenuated total reflection infrared (ATR-IR) spectroscopy during cycling of Li and Mg batteries. The reference phenanthrene quinone and the Li and Mg salts of the hydroquinone monomers were synthesized and their IR spectra were measured. Additionally, IR spectra were calculated using DFT. A comparison of all three spectra allowed us to accurately assign the C=O and C?O? vibration bands and confirm the redox mechanism of the quinone/Li salt of hydroquinone, with radical anion formation as the intermediate product. PFQ/rGO also showed exceptional performance in an Mg battery: A potential of 1.8 V versus Mg/Mg2+, maximum capacity of 186 mAh g?1 (335 Wh kg?1 of cathode material), and high capacity retention with only 8 % drop/100 cycles. Operando ATR-IR spectroscopy was performed in a Mg/organic system, revealing an analogous redox mechanism to a Li/organic cell.

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.

The effect of the donor unit on the optical properties of polymers

A series of donor-acceptor-donor (DAD) type π-conjugated monomers containing 10,11,12,13-tetrahydrodibenzo[a,c]phenazine moiety in the backbone as the acceptor unit and thiophene derivatives as the donor unit were prepared by Stille coupling. Thiophene, 3-hexyl thiophene and 3,4-ethylenedioxythiophene were used as the donor units to understand the effects of donor unit on electrochemical and optoelectronic properties of the resulting polymers. Electroactivity of monomers and redox behavior of their polymers were investigated by cyclic voltammetry. The presence of the strong electron-donating ethylenedioxy groups on the aromatic structure increased electron density on 2,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-10,11,12,13- tetrahydrodibenzo[a,c]phenazine (DTBP), thus the oxidation potential of DTBP shifts to a lower value than that of 2,7-bis(4-hexylthiophen-2-yl)-10,11,12,13- tetrahydrodibenzo[a,c] phenazine (HTBP) and 2,7-di(thiophen-2-yl)-10,11,12,13- tetrahydrodibenzo[a,c]phenazine (TTBP). The electronic band gaps, defined as the onset of the π-π transition, were found to be 2.5 eV for HTBP, 2.0 eV for DTBP and 2.2 eV for TTBP. Both of PDTBP and PTTBP films showed multi-color electrochromism and also fast switching times (1 s) in the visible and NIR regions.

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).

Metal-Free Catalysis: A Redox-Active Donor-Acceptor Conjugated Microporous Polymer for Selective Visible-Light-Driven CO2Reduction to CH4

Achieving more than a two-electron photochemical CO2reduction process using a metal-free system is quite exciting and challenging, as it needs proper channeling of electrons. In the present study, we report the rational design and synthesis of

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

Green light compound based on dibenzophenazine, preparation method and device thereof

The invention belongs to the technical field of photoelectric display devices, and particularly relates to a green light compound based on dibenzophenazine, a preparation method and a device thereof. The invention provides the green light compound based o

Unexpected radical mechanism in a [4+1] cycloaddition reaction

9,10-Phenanthrenequinone monoimines (2,7-R-PQI, R = tBu, H, Br, NO2, 1a-d) undergo a [4+1] cycloaddition reaction with triphenylphosphine to give 2,3-dihydro-2,2,2-triphenylphenanthro[9,10-d]-1,3,2λ5-oxazaphospholes (3a-d). During the reaction, highly colored radicals are formed as intermediates, which were characterized by EPR and UV-vis spectroscopy. The formation rate and the rate of decay of these radicals were determined kinetically. These radicals exhibit high persistency and under inert conditions can be handled conveniently. Based on detailed kinetic and spectroscopic studies and DFT calculations, a plausible mechanism has been proposed. This journal is