16218-32-9

Basic information

• Product Name: 2,7-Diiodophenanthrenequinone
• Synonyms: 2,7-Diiodophenanthrenequinone;2,7-Diiodophenanthrene-9,10-dione;2,7-diiodophenanthrene
• CAS NO: 16218-32-9
• Molecular Formula: C₁₄H₆I₂O₂
• Molecular Weight: 460.01
• Product Categories: Electronic Chemicals
• Mol File: 16218-32-9.mol

Chemical Properties

• Melting Point: 309-310 °C
• Boiling Point: 547.1 °C at 760 mmHg
• Flash Point: 284.7 °C
• Appearance: /
• Density: 2.263
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 2,7-Diiodophenanthrenequinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,7-Diiodophenanthrenequinone(16218-32-9)
• EPA Substance Registry System: 2,7-Diiodophenanthrenequinone(16218-32-9)

Safety Data

• Hazardous Substances Data: 16218-32-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,7-Diiodophenanthrenequinone is utilized as a building block in organic synthesis, particularly for the preparation of dyes, pigments, and pharmaceutical intermediates. Its unique structure and properties make it a versatile component in the creation of a wide range of chemical products.
Used in Chemical Reactions:
2,7-Diiodophenanthrenequinone also serves as a reagent in various chemical reactions, including oxidation and halogenation processes. Its reactivity and the presence of iodine atoms contribute to its effectiveness in these reactions, facilitating the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,7-Diiodophenanthrenequinone is used as a key intermediate in the synthesis of certain drugs. Its role in the development of pharmaceuticals is crucial, as it can influence the properties and effectiveness of the final medicinal products.
Used in Dye and Pigment Industry:
2,7-Diiodophenanthrenequinone is employed as a precursor in the production of dyes and pigments, where its color and stability are highly valued. Its use in this industry contributes to the creation of vibrant and long-lasting colorants for various applications.
Handling and Storage:
Due to its low solubility and reactivity, 2,7-Diiodophenanthrenequinone must be handled and stored with caution. It is essential to maintain a controlled laboratory environment to ensure the safety and integrity of the compound during its use in research and industrial applications.

Upstream product

• 84-11-7 9,10-phenanthrenequinone 

Downstream Products

• 55718-46-2 2,7-Bis-phenylethynyl-phenanthrene-9,10-dione 
• 1425336-92-0 1,4-bis(4-bromophenyl)-2,3-bis(4-tert-butylphenyl)-6,11-diphenyltriphenylene 
• 1425336-87-3 1,4-bis(4-bromophenyl)-2,3,6,11-tetraphenyltriphenylene 
• 1425336-79-3 1,4-bis(4-bromophenyl)-2,3-bis(4-(tert-butyl)phenyl)-6,11-diiodotriphenylene 
• 1425336-75-9 1,4-bis(4-bromophenyl)-6,11-diiodo-2,3-diphenyltriphenylene 
• 1310727-36-6 2,7-bis(4-tert-octylphenylethynyl)-dibenzo[a,c]phenazine 
• 1310726-92-1 2,7-bis(phenylethynyl)phenanthrene-9,10-di(ethyleneglycol)ketal 
• 1310727-17-3 2,7-bis(4-tert-octylphenylethynyl)-phenanthrene-9,10-dione 
• 1310727-09-3 2,7-bis(4-tert-octylphenylethynyl)-9,10-dimethoxyphenanthrene 
• 1257331-74-0 C₃₁H₂₀I₂O₃ 
• 1220107-35-6 2,7-bis((5-phenacyl)thiophen-2-yl)-9,10-phenanthrenequinone 
• 1220107-33-4 2,7-bis((5-perfluorophenacyl)thiophen-2-yl)-9,10-phenanthrenequinone 
• 1192340-23-0 10,12-bis(4-tert-butylphenyl)-2,7-diiododibenzo[f,h]thieno[3,4-b]quinoxaline 
• 690258-69-6 2,7-bis-(4-ethynyl(thioacetyl)benzene)-9,10-bis(tert-butyldimethylsiloxy)phenanthrene 

Relevant articles and documents

The extension of conjugated system in pyridyl-substituted monoazatriphenylenes for the tuning of photophysical properties

We propose a method for the synthesis of diaryl-substituted pyridylmonoazatriphenylenes by the heterocyclization reaction of dihalosubstituted phenanthrenequinones with pyridine-2-carboxylic acid amidrazone, followed by aza-Diels-Alder reaction and Suzuki cross coupling. The obtained compounds showed more promising photophysical properties, compared to non-arylated analogs.

Bipolar highly solid-state luminescent phenanthroimidazole derivatives as materials for blue and white organic light emitting diodes exploiting either monomer, exciplex or electroplex emission

Four phenanthroimidazole-based bipolar compounds having electron-donating carbazole or diphenylamino moieties were synthesized and characterized. All compounds form glasses and exhibit high glass transition temperatures ranging from 183 to 239 °C. Solid state blue emission was detected for all synthesized compounds and quantum yields in solid state reached 0.55. Room temperature hole and electron mobilities in the layers of phenanthroimidazole derivatives reached 3.14 × 10?4 and 5.69 × 10?4 cm2/V·s, respectively, at an electric field of 3.6 × 105 V/cm. Quantum chemical calculations on the molecular level were employed to interpret optical, photophysical and photoelectrical properties of the compounds. Due to the efficient blue solid-state emission and ambipolar charge transport the phenanthroimidazole-based derivatives were used for the preparation of non-doped emitting layers of blue OLEDs. The electroplex forming properties of the compounds were observed in a host:guest emitting layer with a commercial hole-transporting material 4,4′-cyclohexylidenebis [N,N-bis(4-methylphenyl)benzenamine]. Two most promising phenanthroimidazole-based compounds were used for the fabrication of white OLEDs which were based on both fluorescence and either electroplex or exciplex emissions. The best almost blue and white OLEDs were characterized by maximal current efficiency of 1.3 and 5.3 cd/A, power efficiency of 0.8 and 1.7 lm/W, and external quantum efficiency of 0.95 and 2.9 %.

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).

Rechargeable Aluminum Organic Batteries

Disclosed herein are rechargeable aluminum organic batteries and active materials used therein. The cathodic materials used herein comprise a macrocycle comprising a substituted or unsubstituted phenanthrenequinone unit and a graphite flake.

The extension of conjugated system in pyridyl-substituted monoazatriphenylenes for the tuning of photophysical properties

We propose a method for the synthesis of diaryl-substituted pyridylmonoazatriphenylenes by the heterocyclization reaction of dihalosubstituted phenanthrenequinones with pyridine-2-carboxylic acid amidrazone, followed by aza-Diels-Alder reaction and Suzuki cross coupling. The obtained compounds showed more promising photophysical properties, compared to non-arylated analogs.

Synthesis and photophysics of dibenz[a,c]phenazine derivatives

The synthesis of dipolar dibenz[a,c]phenazine (DBP) derivatives is described. The compounds possess little electronic communication between donor and acceptor units in the ground state regardless of the pattern of substitution. The dipolar derivatives deactivate mostly via electron transfer (eT) under polar conditions. Intersystem crossing is likely to compete for S1 relaxation.

Tuning the singlet-triplet gap in metal-free phosphorescent π-conjugated polymers

Glow in the dark: A tunable singlet-triplet exchange gap arises in optically active conjugated polymers that exhibit both strong fluorescence from the singlet state and pronounced phosphorescence from triplet excitations (see picture). The polymers were incorporated into organic light-emitting diodes (OLEDs).

Phenacyl-thiophene and quinone semiconductors designed for solution processability and air-Stability in high mobility n-channel field-effect transistors www.chemeurj.org

Electron-transporting organic semiconductors (n-channel) for fieldeffect transistors (FETs) that are processable in common organic solvents or exhibit air-stable operation are rare. This investigation addresses both these challenges through rational molecular design and computational predictions of n-channel (FETs) air-stability. A series of seven phenacyl-thiophene-based materials are reported incorporating systematic variations in molecular structure and reduction potential. These compounds are as follows: 5,5?-bis(perfluorophenylcarbonyl)-2,2′:5′,-2″:5″, 2?-quaterthiophene (1), 5,5?-bis-(phenacyl)-2,2′;5′, 2″: 5″,2?-quaterthiophene (2), poly[5,5?- (perfluorophenac-2-yl)-4′,4″-dioctyl-2,2':5',2":5", 2'"-quaterthiophene) (3), 5,5?-bis(perfluorophenacyl)-4,4?- dioctyl-2,2′:5′,2″:5″,2?-quaterthiophene (4), 2,7-bis((5-perfluorophenacyl)thiophen-2-yl)-9,10phenanthrenequinone (5), 2,7-bis[(5phenacyl)thiophen-2-yl]-9,10-phenanthrenequinone (6), and 2,7-bis(thiophen-2-yl)-9,10-phenanthrenequinone, (7). Optical and electrochemical data reveal that phenacyl functionalization significantly depresses the LUMO energies, and introduction of the quinone fragment results in even greater LUMO stabilization. FET measurements reveal that the films of materials 1, 3, 5, and 6 exhibit n-channel activity. Notably, oligomer 1 exhibits one of the highest, μe (up to ≈0.3 Cm 2V-1S-1) values reported to date for a solutioncast organic semiconductor; one of the first n-channel polymers, 3, exhibits μe ≈ 10-6 Cm2V -1S-1 in spin-cast films (μc = 0.02 cm 2 V-1S-1 for drop-cast 1:3 blend films); and rare air-stable n-channel material 5 exhibits n-channel FET operation with μe = 0.015 cm2V-1s-1, while maintaining a large Ion:off= 106 for a period greater than one year in air. The crystal structures of 1 and 2 reveal close herringbone interplanar π-stacking distances (3.50 and 3.43 A, respectively), whereas the structure of the model quinone compound, 7, exhibits 3.48 A cofacial π-stacking in a slipped, donor-acceptor motif.

1,3-Diiodo-5,5-dimethylhydantoin-An efficient reagent for iodination of aromatic compounds

1,3-Diiodo-5,5-dimethylhydantoin in organic solvents successfully iodinates alkylbenzenes, aromatic amines, and phenyl ethers. The reactivity of electrophilic iodine is controlled by acidity of the medium. Superelectrophilic iodine generated upon dissolution of 1,3-diiodo-5,5-dimethylhydantoin in sulfuric acid readily reacts with electron-deficient arenes at 0 to 20°C with formation of the corresponding iodo derivatives in good yields. The structure of electrophilic iodine species generated from 1,3-diiodo-5,5- dimethylhydantoin in sulfuric acid is discussed.

Superactivity and dual reactivity of the system N-iodosuccinimide-H 2SO4 in the iodination of deactivated arenes

Dissolution of N-iodosuccinimide in sulfuric acid gives rise to electrophilic iodine-containing species which are capable of successfully iodinating aromatic compounds with electron-withdrawing substituents in the temperature range from 0 to 20°C. The iodination in sulfuric acid is effected by both protonated N-iodosuccinimide and IOS(O)(OH+)OH intermediate.