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Usage

Uses

Used in Organic Electronic Materials Synthesis:
1,8-dibromo-9H-carbazole is used as a key building block in the synthesis of organic electronic materials. Its chemical structure allows for the creation of functional materials with specific electronic properties, making it an essential component in the development of advanced electronic devices.
Used in Organic Light-Emitting Diodes (OLEDs) Production:
In the OLED industry, 1,8-dibromo-9H-carbazole is utilized as a precursor for the production of electroluminescent materials. Its incorporation into OLEDs enhances their performance, leading to improved display quality and energy efficiency.
Used in Organic Semiconductors Development:
1,8-dibromo-9H-carbazole is employed as a component in the development of organic semiconductors. Its unique properties contribute to the enhancement of charge transport and other electronic characteristics, which are crucial for the performance of semiconductor devices.
Used in Technology Applications:
1,8-dibromo-9H-carbazole is used as a valuable tool in the development of new materials for a variety of technology applications. Its unique chemical structure and properties enable the creation of innovative materials that can be applied in various fields, such as electronics, optoelectronics, and energy storage.

Upstream product

• 16807-11-7 1-bromo-9H-carbazole 
• 86-74-8 9H-carbazole 
• 625385-37-7 1,8-dibromo-3,6-di(tert-butyl)-9H-carbazole 
• 104294-50-0 1,8-dibromo-3,6-dinitro-9H-carbazole 
• 3244-54-0 3,6-dinitro-9H-carbazole 
• 1049017-32-4 3,6-diamino-1,8-dibromocarbazole 

Relevant academic research and scientific papers

A new asymmetric tridentate carbazole ligand: Its preparation and application to Nozaki-Hiyama allylation

The manuscript describes our studies on a newly designed tridentate ligand. The new ligand 1 was successfully synthesized, and it was found that the asymmetric catalysis of Nozaki-Hiyama allylation with ligand 1 affords the product with good enantioselectivity in high yield.

Improved Access to 1,8-Diformyl-carbazoles Leads to Metal-Free Carbazole-Based [2 + 2] Schiff Base Macrocycles with Strong Turn-On Fluorescence Sensing of Zinc(II) Ions

Development of a new and high yielding synthetic route to 1,8-diformyl-carbazoles 3 (3a 3,6-di-tert-butyl substituted; 3b 3,6-unsubstituted) is reported. Use of a Heck coupling reaction, followed by ozonolysis, has greatly facilitated the preparation of these interesting head units in useful quantities. An initial foray into the new generations of Schiff base macrocycles that ready access to these head units (3) opens up, has led to the direct (i.e., metal-free) synthesis of two [2 + 2] macrocycles from 3a or 3b with 1,2-diaminoethane, H2LtBu (4a) and H2LH (4b), respectively, obtained as yellow powders in high yields (87-88%). The dizinc complex [Zn2LH(OAc)2] (5b) was isolated as a bright yellow solid in 83% yield, by 1:2:2 reaction of H2LH with zinc(II) acetate and triethylamine. Aldehydes 3a and 3b, macrocycle H2LH, and complex [Zn2LH(OAc)2] (5b) have been structurally characterized. The carbazole NH makes bifurcated hydrogen bonds with the pair of flanking 1,8-diformyl-moieties in 3, or 1,8-diimine-moieties in H2LH, leading to a flat, all-cis conformation. The stepped conformation of the metal-free macrocycle H2LH is retained in [Zn2LH(OAc)2], despite deprotonation and binding of two zinc(II) centers within the two tridentate pockets. The N3O2 coordination of the zinc ions is completed by one μ1,1- and one μ1,3- bridging acetate anion. Excitation of nanomolar [Zn2LH(OAc)2] in DMF at 335 nm results in clearly visible blue fluorescence (λmax = 460 nm). Further studies on the H2LH macrocycle revealed turn-on fluorescence, with selectivity (over Ca2+, Mg2+ and a range of 3d dications) and nanomolar sensitivity for zinc(II) ions, highlighting one of the many potential applications for these new carbazole-based Schiff base macrocycles.

Halogenated method of aromatic compound

The invention belongs to the field of organic synthesis, and particularly relates to synthesis of aromatic halogens, in particular to arylamine. The invention discloses a synthesis method of a corresponding ortho-halogenated product from aromatic compounds such as carbazole and phenol. The method comprises the following steps: adding a metal sulfonate salt catalyst, aromatic amine, carbazole, phenol and other hydrogen - heteroatom-containing aromatic compound reaction substrates, a halogenation reagent and a reaction solvent at a specific reaction temperature. After the drying agent is dried, the yield of the reaction product and the nuclear magnetic characterization determining structure are determined by column chromatography. The reaction product yield is determined by gas chromatography. By adopting the method, under the cheap metal salt catalyst, a plurality of ortho-substituted brominated and chloro products can be obtained with moderate to excellent yield.

Preparation and study of 1,8-di(pyrid-2′-yl)carbazoles

(Figure Presented) A series of three derivatives of 1,8-di(pyrid-2′- yl)carbazole were prepared by Stille-type coupling of 2-(tri-n-butylstannyl) pyridine with the appropriate 1,8-dibromocarbazole. The carbazoles were prepared by appropriate substitution methodologies on the parent carbazole or by palladium-catalyzed cyclization of di-(p-tolyl)amine to provide the carbazole ring system. An X-ray structure of the di-tert-butyl derivative confirmed that both pyridyl groups were oriented for favorable intramolecular H-bonding to the central N-H. Two orientations of the molecule were found in the unit cell and this observation was corroborated by two N-H stretching bands in the solid state IR. Substitution of N-H by N-D led to increased emission intensity through diminished intramolecular deactivation of the excited state. The di-tert-butyl derivative formed a tridentate complex with Pd(II), which showed a red-shifted band attributed to an intraligand charge transfer state.