13577-26-9

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
4,5-DIBROMO-1,8-NAPHTHALENEDICARBOXYLIC ACID is used as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure and reactivity make it a valuable component in the creation of new and effective compounds for medical and agricultural applications.
Used in Organic Chemistry as a Reagent:
In the field of organic chemistry, 4,5-DIBROMO-1,8-NAPHTHALENEDICARBOXYLIC ACID serves as a reagent for the preparation of different types of compounds. Its versatility in chemical reactions contributes to the advancement of organic synthesis and the development of novel chemical entities.
Used in Flame-Retardant Materials and Textiles:
4,5-DIBROMO-1,8-NAPHTHALENEDICARBOXYLIC ACID is known for its flame-retardant properties, making it an essential component in the manufacturing of fire-resistant materials and textiles. Its inclusion in these products enhances their safety and performance in various applications, particularly in industries where fire safety is a critical concern.
Used in the Manufacturing of Fire-Resistant Materials:
In the manufacturing industry, 4,5-DIBROMO-1,8-NAPHTHALENEDICARBOXYLIC ACID is used as a component in the production of fire-resistant materials. Its flame-retardant properties contribute to the development of materials that can withstand high temperatures and reduce the risk of fire-related incidents.
Safety Precautions:

Upstream product

• 81-30-1 1,4,5,8-naphthalenetetracarboxylic dianhydride 
• 43017-99-8 5,6-dibromo-acenaphthene-1,2-dione 
• 117562-51-3 5,6-dibromoacenaphthene-1,2-diol 
• 19190-91-1 5,6-dibromoacenaphthene 
• 83-32-9 acenaphthene 

Downstream Products

• 187536-95-4 N,N’-bis(2,6-diisopropylphenyl)-terrylene-3,4,11,12-tetracarboximide 
• 1246857-77-1 N-(2,6-diisopropylphenyl)-4,5-dibromonaphthalene-1,8-dicarboximide 
• 1453193-26-4 C₅₂H₄₄N₂O₁₀ 
• 1453193-25-3 C₆₀H₆₀N₂O₄ 
• 1453193-32-2 C₃₇H₃₄BrNO₄ 
• 1453193-31-1 C₇₄H₆₈N₂O₈ 
• 1453193-30-0 C₇₄H₆₆N₂O₈ 
• 1453193-28-6 C₆₆H₅₂N₂O₈ 
• 1453193-27-5 C₆₄H₅₂N₂O₄ 

Relevant academic research and scientific papers

Fluorinated 1,8-naphthalimides: Synthesis, solid structure and properties

Three fluorinated 1,8-napthalimides were synthesized from acenaphthene. Their structures were characterized by NMR and EI-MS analyses. The structures of compounds 1b and 1c were also confirmed by X-ray diffraction analysis, which showed that they possessed different packing models. Their optoelectronic properties were investigated. The results indicated that all of the naphthalimides possess good solubility and low LUMO energy level, which make them good solution processing candidates in n-type semiconductor.

Naphthalimide azacyclo-luminescent material and application thereof

The invention discloses a naphthalimide azacyclo-luminescent material and application thereof. The general structural formula of the naphthalimide azacyclo-luminescent material is descried in the descriptions of the invention. The naphthalimide azacyclo-luminescent material provided by the invention has hybrid local charge transfer state performance; triplet excitons can be effectively utilized through high-energy-state reverse inter-gap jump, so that the electroluminescent performance of a device is improved; meanwhile, the naphthalimide azacyclo-luminescent material provided by the inventionis high in conjugation degree, high in rigidity, high in radiation transition rate and high in luminous efficiency; with the types of aryl and substituent groups changed, the light emitting efficiency and light color of the material can be adjusted, and the material can be used as a guest material and a host material and can be applied to the field of organic electronic display.

Anomalous Halogen-Halogen Interaction Assists Radial Chromophoric Assembly

The design of highly efficient supramolecular architectures that mimic competent natural systems requires a comprehensive knowledge of noncovalent interactions. Halogen bonding is an excellent noncovalent interaction that forms halogen-halogen (X2) as well as trihalogen interacting synthons. Herein, we report the first observation of a symmetric radial assembly of chromophores (R3c space group) composed of a stable hexabromine interacting synthon (Br6) that further push the limits of our understanding on the nature, role, and potential of noncovalent halogen bonding. Contrary to the destabilization proposed for Type-I X2 interactions, Br6-synthon-possessing Type-I X2 interactions exhibit a stabilizing nature owing to the exchange-correlation component. The radial assembly of chromophores is further strengthened by intermolecular through-space charge transfer interaction. Br6-synthon-driven 3-fold symmetric radial assembly render a lattice structure that reminisces the chromophoric arrangement in the light harvesting system 2 of purple bacteria.

Practical Syntheses of Terrylene Chromophores from Naphthalene and Perylene Building Blocks

A facile and efficient method to synthesize terrylene imides, a unique class of chromophores, and their derivatives from commercially available naphthalene and perylene building blocks is reported. We developed an extremely efficient Suzuki/C?H-arylation coupling cascade with Pd2(dba)3/PCy3 (dba=dibenzylidenacetone, Cy=cyclohexyl) as the catalyst and highly soluble naphthalene derivatives as starting materials. This efficiency allows purification via precipitation and crystallization, avoiding time-consuming column chromatography. For the first time, the highly soluble 3,4,11,12-terrylene tetraester was prepared in gram scale with yields up to 75% which thus becomes a versatile starting material for the synthesis of new terrylene derivatives. The presented method not only allows the synthesis of terrylene dyes and pigments, but also presents a route towards perylene and terrylene monoimides which is an advantageous simplification of previously reported synthetic procedures. (Figure presented.).

DOUBLE DONOR FUNCTIONALISATION OF THE PERI-POSITIONS OF PERYLENE AND NAPHTHALENE MONOIMIDE VIA VERSATILE BUILDING BLOCKS

The present invention provides the compounds of formulae (3) and (1) wherein n is 0 or 1, R13 and R14 are the same or different and are selected from the group consisting of NHR310, NR311R312, OR313, SR314 and R315, or R13 and R14 together are selected from the group consisting of (a), (b) and (c), and X is CI, Br of I, and a process for the preparation of compounds of formula (3) comprising the compounds of formula (1) as key intermediates.

Novel dyes based on naphthalimide moiety as electron acceptor for efficient dye-sensitized solar cells

Four novel naphthalimide-based dyes (D-1, D-2, D-3 and D-4) were synthesized and utilized as sensitizers in dye-sensitized solar cells (DSCs), in which the triphenylamine (TPA) or indoline groups, naphthalimide unit and carboxylic group were functionalized as electron donor, acceptor and anchoring group, respectively. The naphthalimide unit was employed as the π-conjugation ring and electron acceptor for effectively realizing intramolecular charge separation in the oxidized states. In the series of dyes, the LUMO orbital is delocalized mainly on naphthalimide moieties, especially on the carbonyl group. Consequently, the LUMO electrons are isolated from the carboxyl anchoring group (-CH2CO2H) due to the presence of the methylene group, which could suppress the electron injection efficiency from the excited dyes to the TiO2 conduction band, thus leading to the inferior efficiencies of 1.10, 1.18, 2.27 and 2.70%, respectively, even though they exhibit broad spectral response and high extinction coefficients.

Soluble and stable zethrenebis(dicarboximide) and its quinone

Soluble and stable zethrenebis(dicarboximide) (1) was synthesized by an in situ Stille cross coupling/transannular cyclization reaction. 1 showed largely improved photostability and solubility compared with the very unstable zethrene and it also exhibited

Sterically fixed dithiolate ligands and their zinc complexes: Derivatives of 1,8-dimercaptonaphthalene

The synthesis of two new dithiols, 1,8-dimercapto-2,7-di(tert-butyl)naphthalene (H2L1) and 1,8-dimercaptonaphthoic anhydride (H2L2), is described. They react with diethylzinc to yield the polymeric complexes L1Zn and L2Zn. L1Zn dissolves in the presence of pyridine to form [L1Zn·py]x, which is presumed to be dimeric. Both L1Zn and L2Zn react with neocuproin. Structure determinations have confirmed the tetrahedral ZnN2S2 coordination in the resulting LZn·neo complexes.

1,2-Derivatives of acenaphthylene. VI. Synthesis and properties of 4-, 3,5-, 5,6-, and 3,5,6-bromo derivatives of acenaphthene-1,2-diol

The acetolysis of the 4-, 3,5-, 5,6-, and 3,5,6-bromo derivatives of 1,2-dibromoacenaphthene leads to the formation of the monoacetates of bromine-substituted acenaphthene-1,2-diols.Esterification of the latter leads to the diacetates, and hydrolysis leads to the corresponding diols.During oxidation of the bromine-substituted acenaphthene-1,2-diols with chromic acid the derivatives of acenaphthylene-1,2-dione and 1,8-naphthalenedicarboxylic acid are formed.