29377-72-8

Usage

Uses

Used in Organic Synthesis:
9H-Carbazole-3,6-dicarboxaldehyde, 9-methylis used as a building block in the synthesis of various pharmaceuticals, dyes, and other organic compounds due to its unique structure and properties.
Used in Optoelectronics and Materials Science:
9H-Carbazole-3,6-dicarboxaldehyde, 9-methylis used in the field of optoelectronics and materials science for its interesting fluorescence properties, making it potentially useful in the development of new organic electronic devices and photoluminescent materials.
Used in Research and Development:
9H-Carbazole-3,6-dicarboxaldehyde, 9-methylis utilized in research and development for exploring its potential applications in various industries, including pharmaceuticals, dyes, and materials science, due to its unique properties and structure.

Upstream product

• 1484-12-4 N-methylcarbazole 
• 93-61-8 N-methyl-N-phenylformamide 
• 68-12-2 N,N-dimethyl-formamide 
• 58246-82-5 3,6-dibromo-9-methyl-9H-carbazole 
• 6825-20-3 3,6-dibromo-9H-carbazole 
• 86-74-8 9H-carbazole 

Relevant academic research and scientific papers

Preparation of novel symmetrical bistetrazole-carbazole derivatives through a one-pot Ugi-azide reaction

A series of new symmetrical tetrazole-based carbazole derivatives starting from the initially generated 3,6-diformyl-N-alkylcarbazoles were successfully synthesized through a one-pot Ugi-azide reaction in moderate to high yields. Simplicity, easily accessible chemicals, mild reaction conditions, and fast separation of the products with the formation of bistetrazole-based carbazole derivatives in one step are some advantages of this method. The structure of the products was characterized and confirmed by using spectroscopic techniques such as 1H NMR, 13C NMR, FT-IR, and MS spectroscopy.

A cucurbituril/polysaccharide/carbazole ternary supramolecular assembly for targeted cell imaging

A carbazole derivative (G) was synthesized as a photosensitizer to complex with cucurbit[8]uril, resulting in a nanocube with emission at 662 nm for lysosome cell imaging. Furthermore, the alkyl chain on G was included by α-cyclodextrine-modified hyaluronic acid for further assembly, affording a system targeted to cancer cells.

Dual-site fluorescent probe for highly selective and sensitive detection of sulfite and biothiols

A dual-site fluorescent probe with double bond and aldehyde as reactive sites, was designed for the selective detection of sulfite and biothiols. Sulfite reacts with conjugate bond selectively, while Cys responses with aldehyde and GSH occurs substitution reaction. Different interactions cause different absorption and fluorescence responses. Moreover, it could be further applied in imaging in living cells.

Interaction of bisbenzimidazole-substituted carbazole derivatives with G-quadruplexes and living cells

G-quadruplex (G4) ligands have potential as chemotherapeutic agents because of the important roles of G4s in regulation of genomic function. Previously, we have developed a fluorescent probe (termed as BPBC) with excellent selectivity to parallel G4s, which possesses a V-shaped bisbenzimidazole-substituted carbazole planar core and two methylpiperazine side arms. Here, we further investigated the interactions of BPBC derivatives with different DNA and living cells. The spectral analysis showed that non-substituted bisbenzimidazole-substituted carbazole (7c) and bisdimethylamino-substituted 7c (7b) exhibited good selectivity to parallel G4s. The binding affinities of BPBC derivatives to parallel G4s were BPBC > 7b 7c. BPBC and 7b entered living cells and mainly located in the cytoplasma and nucleoli; 7c mainly located in the lysosome. BPBC exhibited the highest cytotoxicity with IC50 around 1 μM. Our results suggest that the bisbenzimidazole-substituted carbazole core is the key factor for selectively binding BPBC derivatives to parallel G4s; the side arms can change their affinity to specific G4s, as well as their interaction with cells. Further optimization of the side arms will provide the opportunity to obtain chemotherapeutic agents targeting specific G4s in cells.

Carbazole-based 1D and 2D hemicyanines: Synthesis, two-photon absorption properties and application for two-photon photopolymerization 3D lithography

One and two dimensional (1D and 2D) carbazole based hemicyanines, where methyl pyridinium, methyl indolium and methyl benzothiazolium were used as acceptor group, were synthesized by Knoevenagel condensation. One-photon absorption, fluorescence and two-photon fluorescence spectra were investigated. The experimental results indicated that the different ionic acceptors affect their one-photon and two-photon properties. Among them, 2D methyl pyridinium carbazole derivatives exhibited low quantum yields and large two-photon absorption cross sections more than 1600 GM. The synthesized compounds were used as photoinitiator of two-photon photopolymerization (TPP), and three-dimensional (3D) microstructure was successfully fabricated by TPP 3D lithography. They could be utilized as effective two-photon polymerization photoinitiators. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Vilsmeier reaction on carbazole: Theoretical and experimental aspects

The pathway of the Vilsmeier reaction on carbazole has been studied by AM1 semiempirical MO calculations, which includes the characterization of the various transition structures; an experimental study of the actual reaction shows the formation of diformyl derivative along with a monoformyl derivative.