633-68-1

Usage

Uses

Used in Dye Industry:
2,3-Dibromoanthraquinone is used as a dyestuff for its vivid coloration properties. Its ability to impart intense color makes it a valuable component in the production of various dyes and pigments.
Used in Chemical Research:
2,3-Dibromoanthraquinone is used as a research chemical for studying the properties and reactions of anthraquinone derivatives. Its unique structure allows for exploration of its potential applications in various chemical processes and synthesis.
Used in Pharmaceutical Industry:
2,3-Dibromoanthraquinone is used as an intermediate in the synthesis of pharmaceutical compounds. Its chemical structure can be further modified to create new drugs with potential therapeutic applications.
Used in Material Science:
2,3-Dibromoanthraquinone is used as a component in the development of new materials with specific properties, such as improved stability or enhanced performance in certain applications. Its unique chemical structure contributes to the overall characteristics of the materials being developed.

Upstream product

• 6337-00-4 2-amino-3-bromoanthraquinone 
• 861789-90-4 2,3,10-tribromo-10-nitro-anthrone 
• 108-88-3 toluene 
• 3141-26-2 3,4-dibromothiophene 
• 130-15-4 [1,4]naphthoquinone 
• 583-53-9 2,3-dibromobenzene 
• 89088-96-0 3,4-dibromothiophene 1,1-dioxide 
• 861299-42-5 2,3,9-tribromo-10-isopropyl-anthracene 
• 861792-18-9 9-ethyl-2,3,10-tribromo-anthracene 
• 871879-64-0 2,3,9,10-tetrabromoanthracene 
• 157528-08-0 2-(3,4-Dibromobenzoyl)benzoic acid 
• 85-44-9 phthalic anhydride 
• 861294-27-1 9-benzyl-2,3,10-tribromo-anthracene 
• 1066-30-4 chromium(lll) acetate 

Downstream Products

• 72-48-0 1,2-dihydroxy-9,10-anthracenedione 
• 1358517-42-6 C₃₀H₁₄O₂ 
• 1413861-38-7 C₂₆H₁₅BrO₂ 
• 6363-19-5 2,3-diphenylanthracene-9,10-dione 
• 84-65-1 9,10-phenanthrenequinone 
• 605-42-5 2,7-dibromo-9,10-anthraquinone 
• 120-12-7 anthracene 

Relevant academic research and scientific papers

New blue emitting material with asymmetric limb structure

The new assymmetric limb-structured blue light emitting material, composed of anthracene main core, naphthalene units at 9, 10-position of anthracene and xylene units at 2,3-positon of anthracene, was designed and synthesized. The three-dimensional structure from theoretical calculation was characterized to elucidate non-copolar structure with inhibited intermolecular interaction. The limb-structured blue material was thermally stable up to 373°C with Tg of 143°C. ITO/TAPC/CBP (3% BMPNA)/Bphen/LiF/Al device exhibits the maximum quantum efficiency of 3.42% and maximum current efficiency of 3.07 cd/A with deep blue emission of (0.141, 0.115) CIE coordinates.

Trifluoromethylation of Anthraquinones for n-Type Organic Semiconductors in Field Effect Transistors

This study puts forth a new design of n-type organic semiconductors, which has trifluoromethylethynyl groups attached to 9,10-anthraquinone at different positions. These electron-deficient anthraquinones are synthesized by trifluoromethylation of the corresponding trimethylsilyl-protected alkynes with fluoroform-derived CuCF3, and their ?-πstacking in the crystals is tunable by varying the positions of trifluoromethylethynyl groups. It is found that most of these trifluoromethylated anthraquinones function as n-type semiconductors in solution-processed field effect transistors with electron mobility of up to 0.28 cm2 V-1 s-1

New limb structured blue light emitting materials for OLEDs

We designed new three limb structured anthracene derivatives, PNA, NNA and FNA, which are composed of an anthracene core and naphthalene units at the 9,10-positions of anthracene and phenyl, naphthalene and fluorene units at the 2,3-positons of anthracene. The effect of the introduced limbs on the 2,3,9,10-positions of anthracene was studied. The doped EL devices using ADN as a host and (3% PNA or NNA or FNA) as a dopant showed similar maximum quantum efficiency of 3.9%-4.3% with high color purity of (0.15, 0.13).

(Aza)Acenes Share the C2 Bridge with (Anti)Aromatic Macrocycles: Local vs. Global Delocalization Paths

A strong conjugation present in fused systems plays a crucial role in tuning of the properties that would be showing a dependence on the efficiency of π-electrons coupling. The π-cloud available in the final structure can be drastically influenced by a side- or a linear fusion of unsaturated and conjugated hydrocarbons. The linear welding of naphthalene/anthracene or quinoxaline/benzo[g]quinoxaline with triphyrin(2.1.1) gives structures where the competition between local and global delocalization is distinguished. The aromatic character observed in skeletons strongly depends on the oxidation state of the macrocyclic flanking and is either extended over the whole system or kept as a composition of local currents (diatropic and paratropic) of incorporated units. The hybrid systems show the properties derived from the π-conjugations that interlace one another but also show a significant independence of (aza)acene subunits reflected in the observed spectroscopic properties.

Synthesis and photophysical properties of dinaphtho[2,3-b:2′,3′-i]dihydrophenazine derivatives

A dinaphtho[2,3-b:2′,3′-i]dihydrophenazine (DNP) derivative was synthesized by Buchwald-Hartwig cross-coupling, and its electronic spectrum was compared with that of dinaphtho[b,i]dihydrophenazine-5,18-dione (DNP-dione) as an anthraquinone analog. An absorption band of DNP is attributed to extension of π-conjugation over the entire molecule via the N atom. DNP-dione showed a broad absorption band in the range 450–490 nm due to intramolecular charge-transfer interactions. Additionally, the absolute fluorescence quantum yield of DNP was larger than that of DNP-dione. DNP-dione exhibited reversible oxidation peaks and a similar oxidation potential to DNP, since there are very weak electronic interactions between the anthracene and anthraquinone units across the N atoms with the 4-octyloxyphenyl substituent.

NOVEL ORGANIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING SAME

A novel organic compound suitably used for a green- light-emitting device and an organic light-emitting device are provided. An organic light-emitting device and an image display apparatus containing a naphtho [2 ', 3 ' : 5, 6] indeno [1, 2, 3- cdjpyrene derivative represented by general formula (1) as a dopant : wherein in general formula (1), R1 to R16 are each independently selected from a hydrogen atom, a halogen atom, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkoxy groups, substituted or unsubstituted amino groups, substituted or unsubstituted aryl groups, and substituted or unsubstituted heterocyclic groups, and at least one of R3, R4, R9, and R10 is selected from substituted or unsubstituted aryl groups and substituted or unsubstituted heterocyclic groups.

NOVEL FUSED POLYCYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING ELEMENT

A fused polycyclic compound is represented by general formula [1]: [Chem. 1] wherein at least one of R1 to R16 is selected from a halogen atom, an alkyl group having 1 to 20 carbon atoms, a substituted amino group, an aryl group which may have a substituent, and a heterocyclic group which may have a substituent. An organic light-emitting element includes the fused polycyclic compound.

An efficient synthesis of substituted anthraquinones and naphthoquinones

An efficient synthesis of 6,7-disubstituted naphthoquinones and 2,3,6,7-tetrasubstituted anthraquinones were developed using the reaction of thiophene dioxides and benzoquinone and naphthoquinone derivatives, respectively.

REAGENT FOR DETERMINING SINGLET OXYGEN

Compounds useful as agents for measurement of singlet oxygen, which are represented by the following general formula (I): wherein R1, R2, R3, R4, R5, and R6 independently represent a hydrogen atom, a halogen atom, a C1-6 alkyl group, or a C1-6 alkoxyl group, R7 and R8 independently represent a C1-4 alkyl group, and R9 represents a hydrogen atom, a C1-12 alkanoyl group, or acetoxymethyl group, or salts thereof.

Rational design of fluorescein-based fluorescence probes. Mechanism-based design of a maximum fluorescence probe for singlet oxygen

Fluorescein is one of the best available fluorophores for biological applications, but the factors that control its fluorescence properties are not fully established. Thus, we initiated a study aimed at providing a strategy for rational design of functional fluorescence probes bearing fluorescein structure. We have synthesized various kinds of fluorescein derivatives and examined the relationship between their fluorescence properties and the highest occupied molecular orbital (HOMO) levels of their benzoic acid moieties obtained by semiempirical PM3 calculations. It was concluded that the fluorescence properties of fluorescein derivatives are controlled by a photoinduced electron transfer (PET) process from the benzoic acid moiety to the xanthene ring and that the threshold of fluorescence OFF/ON switching lies around -8.9 eV for the HOMO level of the benzoic acid moiety. This information provides the basis for a practical strategy for rational design of functional fluorescence probes to detect certain biomolecules. We used this approach to design and synthesize 9-[2-(3carboxy-9,10-dimethyl)anthryl]-6-hydroxy-3H-xanthen-3-one (DMAX) as a singlet oxygen probe and confirmed that it is the most sensitive probe currently known for 1O2. This novel fluorescence probe has a 9,10-dimethylanthracene moiety as an extremely fast chemical trap of 1O2. As was expected from PM3 calculations, DMAX scarcely fluoresces, while DMAX endoperoxide (DMAX-EP) is strongly fluorescent. Further, DMAX reacts with 1O2 more rapidly, and its sensitivity is 53-fold higher than that of 9-[2-(3-carboxy-9,10-diphenyl)anthryl]-6-hydroxy-3H-xanthen-3-ones (DPAXs), which are a series of fluorescence probes for singlet oxygen that we recently developed. DMAX should be useful as a fluorescence probe for detecting 1O2 in a variety of biological systems.