10420-20-9

Basic information

• Product Name: 9H-Carbazole, 9-(4-bromobutyl)-
• Synonyms: 9H-Carbazole, 9-(4-bromobutyl)-
• CAS NO: 10420-20-9
• Molecular Formula: C₁₆H₁₆BrN
• Molecular Weight: 302.20894
• EINECS: 200-258-5
• Mol File: 10420-20-9.mol
• Article Data: 54

Chemical Properties

• Melting Point: 109 °C
• Appearance: /
• CAS DataBase Reference: 9H-Carbazole, 9-(4-bromobutyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 9H-Carbazole, 9-(4-bromobutyl)-(10420-20-9)
• EPA Substance Registry System: 9H-Carbazole, 9-(4-bromobutyl)-(10420-20-9)

Safety Data

• Hazardous Substances Data: 10420-20-9(Hazardous Substances Data)

Usage

Uses

9-(4-Bromobutyl)-9H-carbazole is a useful intermediate used in the preparation of arbazole imidazolium salts with antitumor activity.

Upstream product

• 942-01-8 1,2,3,4-tetrahydrocarbazole 
• 108-94-1 cyclohexanone 
• 100-63-0 phenylhydrazine 
• 86-74-8 9H-carbazole 
• 110-52-1 1,4-dibromo-butane 

Downstream Products

• 1236350-50-7 4-[p-[N-(4-(9-carbazole))butyl-N-phenyl]aniline]-6-phenyl-2,2'-bipyridine 
• 884851-06-3 ethyl 4-[4-(9H-carbazol-9-yl)butoxy]benzoate 

Relevant articles and documents

Organic Nanocrystals with Bright Red Persistent Room-Temperature Phosphorescence for Biological Applications

Persistent room-temperature phosphorescence (RTP) in pure organic materials has attracted great attention because of their unique optical properties. The design of organic materials with bright red persistent RTP remains challenging. Herein, we report a n

Synthesis and spectroscopic characterisation of (E)-2-(2-(9-(4-(1H-1,2,4- triazol-1-yl)butyl)-9H-carbazol-3-yl)vinyl)-3-ethylbenzo[d]thiazol-3-ium, a new ligand and potential DNA intercalator

Three new compounds based on carbazole planar skeleton were synthesised. Among them there is a new ligand and a potential DNA intercalator which contains a benzothiazolium moiety connected to the carbazole ring by a vinyl bridge. The absorption and emission spectral properties of this new ligand have been studied by spectroscopic methods.

An attempt to modify nonlinear optical effects of polyurethanes by adjusting the structure of the chromophore moieties at the molecular level using "click" chemistry

The modification of the nonlinear optical effects (NLO) properties of polyurethanes by adjusting the structure of chromophore moieties at the molecular level by introducing different size of isolation spacers, was illustrated. One of the major problems arising while optimizing organic NLO materials is to efficiently translate the large β values of the organic chromophores into high macroscopic NLO activities of polymers. The isolation parts in the chromophore moieties can weaken the strong intermolecular electrostatic interaction to enhance the resultant macroscopic NLO effect of polymers. The dynamic thermal stabilities of the NLO activities of the polymers are investigated by depoling experiments where the real time decays of their SHG signals are monitored. The results show that the NLO properties do not always increase accompanying with the entanglement of the isolation groups linked to the corresponding chromophore moieties.

Multi-layered hybrid perovskites templated with carbazole derivatives: Optical properties, enhanced moisture stability and solar cell characteristics

Research into 2D layered hybrid perovskites is on the rise due to the enhanced stability of these materials compared to 3D hybrid perovskites. Recently, interest towards the use of functional organic cations for these materials is increasing. However, a vast amount of the parameter space remains unexplored in multi-layered (n > 1) hybrid perovskites for solar cell applications. Here, we incorporate carbazole derivatives as a proof of concept towards the use of tailored functional molecules in multi-layered perovskites. Films of low-n carbazole containing perovskites show high photoconductivity half-lifetimes. Higher-n (?n? = 40) multi-layered perovskite films possess charge carrier diffusion lengths comparable to MAPI thin films. Solar cells containing these materials have comparable efficiencies to our MAPI and phenethylammonium (PEA)-containing multi-layered perovskite reference devices. Moisture stability tests were performed both at the material and device levels. In comparison to MAPI and PEA-based materials and solar cells, the addition of a small percentage of the carbazole derivative to the perovskite material significantly enhances the moisture stability.

Design, synthesis and biological activity evaluation of novel carbazole-benzylpiperidine hybrids as potential anti Alzheimer agents

Alzheimer's disease (AD) as the most common form of dementia in aged people, is an intricate neurodegenerative disease. Therefore, a novel strategy so-called multi-target-directed ligand has received much attention for the effective treatment of AD. In this study a series of novel carbazole-benzylpiperidine hybrids 9a-m was designed, synthesized and evaluated as acetylcholinesterase and butyrylcholinesterase inhibitors. Moreover, some of these compounds were evaluated for anti β-secretase (BACE1) activity and metal chelation properties. Among the synthesized compounds, compounds 9b (IC50 = 16.5 μM for AChE and IC50 = 0.59 μM for BuChE) and 9c (IC50 = 26.5 μM for AChE and IC50 = 0.18 μM for BuChE) showed the highest inhibitory activity against acetylcholinesterase and butyrylcholinesterase. Furthermore, these compounds (9b and 9c) displayed interaction with Zn2+ ion and compound 9c showed moderate inhibitory activity against BACE1 (24.5% at 50 μM). Kinetic and docking studies exhibited that these compounds likely act as a non-competitive inhibitor able to interact with the catalytic active site (CAS) and peripheral anionic site (PAS) of acetylcholinesterase simultaneously.

External Heavy-Atom Effect via Orbital Interactions Revealed by Single-Crystal X-ray Diffraction

Enhanced spin-orbit coupling through external heavy-atom effect (EHE) has been routinely used to induce room-temperature phosphorescence (RTP) for purely organic molecular materials. Therefore, understanding the nature of EHE, i.e., the specific orbital interactions between the external heavy atom and the luminophore, is of essential importance in molecular design. For organic systems, halogens (e.g., Cl, Br, and I) are the most commonly seen heavy atoms serving to realize the EHE-related RTP. In this report, we conduct an investigation on how heavy-atom perturbers and aromatic luminophores interact on the basis of data obtained from crystallography. We synthesized two classes of molecular systems including N-haloalkyl-substituted carbazoles and quinolinium halides, where the luminescent molecules are considered as "base" or "acid" relative to the heavy-atom perturbers, respectively. We propose that electron donation from a π molecular orbital (MO) of the carbazole to the σ? MO of the C-X bond (π/σ?) and n electron donation to a π? MO of the quinolinium moiety (n/π ?) are responsible for the EHE (RTP) in the solid state, respectively.

An efficient ultrasound-assisted synthesis of n-alkyl derivatives of carbazole, indole, and phenothiazine

Heterocyclic compounds bearing an acidic hydrogen atom attached to nitrogen such as carbazole, indole, and phenothiazine can be efficiently alkylated in DMSO or N,N-DMF under ultrasonic irradiation in the presence of potassium hydroxide as a base. In almost all cases, a dramatic reduction of the reaction time results and a clear yield increase accompanied by an improved quality of the products occurs.

Wet-process feasible novel carbazole-type molecular host for high efficiency phosphorescent organic light emitting diodes

Wet-process organic light-emitting diodes (OLEDs) are crucial to realize cost-effective and large-area roll-to-roll fabrication of high quality displays and lightings. In this study, a wet-process feasible carbazole based host material, 2-[4-(carbazol-9-yl)butyloxy]-9-[4-(carbazol-9-yl)butyl]carbazole (6), is synthesized, and two other carbazole hosts, 2-[5-(carbazol-9-yl)pentyloxy]-9-[5-(carbazol-9-yl)pentyl]carbazole (7) and 2-[6-(carbazol-9-yl)hexyloxy]-9-[6-(carbazol-9-yl)hexyl]carbazole (8) are also synthesized for comparison. All the three host materials exhibit high triplet energy, and possess high solubility in common organic solvents at room temperature. On doping a green phosphorescent emitter fac tris(2-phenylpyridine)iridium (Ir(ppy)3) into host 6, the device shows an efficacy of 51 lm W-1 and a current efficiency of 52 cd A-1 at 100 cd m-2 or 30 lm W-1 and 40.7 cd A-1 at 1000 cd m-2. The high efficiency may be attributed to the host possessing an effective host-to-guest energy transfer, the ability for excitons to generate on both host and guest, and excellent film integrity.

Pressure-induced phosphorescence enhancement and piezochromism of a carbazole-based cyclic trinuclear Cu(i) complex

Interest in piezochromic luminescence has increased in recent decades, even though it is mostly limited to pure organic compounds and fluorescence. In this work, a Cu3Pz3(Cu3, Pz: pyrazolate) cyclic trinuclear complex (CTC) with two different crystalline polymorphs, namely1aand1b, was synthesized. The CTC consists of two functional moieties: carbazole (Cz) chromophore andCu3units. In crystals of1a, discreteCz-Cu3-Cu3-Czstacking was found, showing abnormal pressure-induced phosphorescence enhancement (PIPE), which was 12 times stronger at 2.23 GPa compared to under ambient conditions. This novel observation is ascribed to cooperation between heavy-atom effects (i.e., from Cu atoms) and metal-ligand charge-transfer promotion. The infinite π-π stacking ofCzmotifs was observed in1band it exhibited good piezochromism as the pressure increased. This work demonstrates a new concept in the design of piezochromic materials to achieve PIPEviacombining organic chromophores and metal-organic phosphorescence emitters.

Investigating carbazole jacketed precursor dendrimers: Sonochemical synthesis, characterization, and electrochemical crosslinking properties

Precursor carbazole terminated dendrons and dendrimers up to generation four (G4-D) were synthesized using a convergent approach. Sonication as a means of facilitating organic reactions in dendrimer chemistry was explored resulting in very facile and very fast (up to 50x) reaction times compared to those using traditional reflux conditions. The limits of peripheral group functionality were explored as a function of generation. The electrochemical cross-linking of the dendrimers as thin films revealed unusual cyclic voltammetry (CV) behavior depending upon the generations, which were significantly different from their linear counterpart, Poly(N-vinylcarbazole) (PVK). G1-D showed a higher extent of intermolecular cross-linking while G4-D showed a higher extent of intramolecular cross-linking. The formed films were optically clear and possess superior energy band gap properties making them an alternative candidate over PVK for future hole-transport layer materials in electro-optical devices.

Motion-Induced Changes in Emission as an Effective Strategy for the Ratiometric Probing of Human Serum Albumin and Trypsin in Biological Fluids

Herein, we report the formation of a highly luminescent, pH-sensitive, thermoreversible nanoaggregate in pure aqueous medium through the self-agglomeration of carbazole-based amphiphiles. The self-assembly process restricted the intramolecular motion of the molecules and induced a change in its emission signal from blue to cyan, owing to an aggregation-induced emission (AIE) effect. A similar type of ratiometric response was also observed in the presence of human serum albumin (HSA). However, in this case, the molecular motion of the flexible fluorescent probe was restricted by its embedded microenvironment, owing to a motion-induced change in emission (MICE) effect, not by aggregation. Moreover, the probe showed quite high selectivity for HSA over other serum albumin proteins. Our carbazole-based fluorescent probes are a unique example of the ratiometric sensing of HSA through the sole involvement of reversible noncovalent interactions. Considering the important of HSA in clinical diagnosis, a wide range of biological fluids, such as human urine, saliva, and plasma, were screened to analyze their HSA content. In addition, this system was also employed for the detection of trypsin at subnanomolar concentrations through the digestion of HSA.

Intramolecular Triplet Energy Transfer. 3. A Carbazole-Naphthalene System Having Short Chain Length Methylene Spacer Units

Laser flash photolysis was used to measure rates of triplet energy transfer from carbazole (Cz) to naphthalene (Np) in rigid solutions of Cz-(CH2)n-Np, where n=4, 5, 6 or 8.The results are interpreted in terms of Dexter's equation and a model which allows for a distribution of donor-acceptor distances for a given n.The distribution was calculated using an arithmetic mean of a center-to-center and closest edge distance between the donor and acceptor chromophores.This model provided the transfer rate for all the compounds tested, and the results indicated a through-space mechanism.

Synthesis and Characterization of Compounds Based on Carbazole and Sulfone Groups

Two compounds containing carbazole and sulfone groups with different alkyl chain lengths have been designed and synthesized. The sulfone group has strong absorption characteristics and the alkoxy chain and carbazole group are electron-rich, forming D-δ-A-type symmetrical molecules. The molecules have the characteristics of charge transfer and high thermal stability, and the molecules stack to form a layered staggered stack, reducing the intermolecular π–π interactions. The target compounds also exhibit strong ultraviolet-fluorescent emission in the solid state at room temperature, and they are expected to be good luminescent materials. Graphical Abstract: [Figure not available: see fulltext.]