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9-(8-bromooctyl)carbazole is a chemical compound belonging to the carbazole family, with the molecular formula C26H25BrN. It is distinguished by the presence of a bromo-substituted octyl chain attached to the carbazole ring, which endows it with unique structural and electronic properties.

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  • 127271-60-7 Structure
  • Basic information

    1. Product Name: 9-(8-bromooctyl)carbazole
    2. Synonyms: 9-(8-bromooctyl)carbazole
    3. CAS NO:127271-60-7
    4. Molecular Formula: C20H24BrN
    5. Molecular Weight: 358.31526
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 127271-60-7.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 480.0±37.0 °C(Predicted)
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: 1.22±0.1 g/cm3(Predicted)
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: 9-(8-bromooctyl)carbazole(CAS DataBase Reference)
    10. NIST Chemistry Reference: 9-(8-bromooctyl)carbazole(127271-60-7)
    11. EPA Substance Registry System: 9-(8-bromooctyl)carbazole(127271-60-7)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 127271-60-7(Hazardous Substances Data)

127271-60-7 Usage

Uses

Used in Organic Electronics:
9-(8-bromooctyl)carbazole is used as a hole-transporting material for its strong electron donor properties, making it suitable for applications in organic electronics.
Used in Optoelectronic Devices:
In optoelectronics, 9-(8-bromooctyl)carbazole is utilized as a component due to its ability to facilitate the transport of holes, which is crucial for the performance of these devices.
Used in Photovoltaic Applications:
9-(8-bromooctyl)carbazole is studied for its potential use in photovoltaics, where its properties may enhance the efficiency of solar cells by improving charge transport.
Used in Organic Light-Emitting Diodes (OLEDs):
In the manufacturing of OLEDs, 9-(8-bromooctyl)carbazole serves as a component that contributes to the device's light-emitting capabilities, taking advantage of its electron-donating and hole-transporting characteristics.
Used in Research and Development:
9-(8-bromooctyl)carbazole is also used as a subject of study in research for further exploration of its potential applications across various technological and industrial fields, given its unique structure and properties.

Check Digit Verification of cas no

The CAS Registry Mumber 127271-60-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,7,2,7 and 1 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 127271-60:
(8*1)+(7*2)+(6*7)+(5*2)+(4*7)+(3*1)+(2*6)+(1*0)=117
117 % 10 = 7
So 127271-60-7 is a valid CAS Registry Number.

127271-60-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 9-(8-bromooctyl)carbazole

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:127271-60-7 SDS

127271-60-7Downstream Products

127271-60-7Relevant articles and documents

Intramolecular Triplet Energy Transfer of the System Having Donor and Acceptor at the Chain Ends. 2. The Carbazole-Naphthalene System

Katayama, Hideaki,Ito, Shinzaburo,Yamamoto, Masahide

, p. 10115 - 10119 (1992)

Intramolecular triplet-triplet (T-T) energy transfer in a series of polymethylene chains having a carbazole group as an energy donor and a naphthalene group as an energy acceptor has been studied by phosphorescence measurement.The phosphorescence decay curves were analyzed by Dexter's equation in which the distribution of donor-acceptor (D-A) distance was calculated by the conformational energy analysis.The results of the simulation were in fairly good agreement with the experimentally observed decay curves.We conclude that the through-space mechanism is adequate for intramolecular T-T energy transfer of the flexible D-A molecules.

Formation of poly(9,9-dioctylfluorene) β-phase by incorporating aromatic moiety in side chain

Zhao, Sen,Liang, Junfei,Guo, Ting,Wang, Yu,Chen, Xuan,Fu, Denghao,Xiong, Junbin,Ying, Lei,Yang, Wei,Peng, Junbiao,Cao, Yong

, p. 130 - 138 (2016)

Two novel polyfluorene-based blue-light emitting copolymers consisting of aromatic carbazole or dibenzothiophene-S,S-dioxide (SO) moiety in side chain are designed and synthesized based on a palladium-catalyzed Suzuki polymerization. The UV–vis absorption, photoluminescence characteristics and wide-angle X-ray diffraction measurements of the resulting copolymers demonstrate that the incorporation of such aromatic units can induce the formation of the β-phase. The resulting copolymers consisting of aromatic units exhibit improved electroluminescence properties relative to the pristine PFO film. A maximum luminous efficiency of 2.25?cd?A?1 with Commission Internationale de l'Eclairage coordinates of (0.17, 0.09) is obtained from the light-emitting device based on the copolymer consisting of SO unit (PFO-SO). Device based on copolymer PFO-SO also exhibits stable electroluminescent spectra and relatively low roll-off of luminous efficiency at high current densities. These observations indicate that the incorporation of aromatic moiety in side chain is a promising strategy to obtain stable blue-light-emitting polyfluorenes with enhanced efficiency.

Synthesis and properties of a new class of aggregation-induced enhanced emission compounds: Intense blue light emitting triphenylethylene derivatives

Liu, Cong,He, Wen,Shi, Guang,Luo, Haiyuan,Zhang, Song,Chi, Zhenguo

, p. 154 - 161 (2015)

A new series of fluorescent carbazole derivatives bearing linear alkyl chains with aggregation-enhanced emission properties have been synthesized. The compounds were fully characterized by elemental analysis, mass spectrometry and nuclear magnetic resonance spectroscopy. The compounds have high decomposition temperatures of 310-361 °C and exhibit intense blue fluorescence with maximum emission wavelengths at 445-473 nm. All the compounds emit weakly in solutions, but become strong emitters in the aggregated state and the photoluminescence intensity values increase up to 14 fold. An emitting device was fabricated using one of the compounds in the emitting layer which exhibits good electroluminescent performance with a blue emission color (λ = 478 nm), a turn-on voltage of 3.6 V and a maximum luminance of 1463 cd/m 2.

N-thioalkylcarbazoles derivatives as new anti-proliferative agents: synthesis, characterisation and molecular mechanism evaluation

Sinicropi, Maria Stefania,Iacopetta, Domenico,Rosano, Camillo,Randino, Rosario,Caruso, Anna,Saturnino, Carmela,Muià, Noemi,Ceramella, Jessica,Puoci, Francesco,Rodriquez, Manuela,Longo, Pasquale,Plutino, Maria Rosaria

, p. 434 - 444 (2018)

Synthetic or natural carbazole derivatives constitute an interesting class of heterocycles, which showed several pharmaceutical properties and occupied a promising place as antitumour tools in preclinical studies. They target several cellular key-points, e.g. DNA and Topoisomerases I and II. The most studied representative, i.e. Ellipticine, was introduced in the treatment of metastatic breast cancer. However, because of the onset of dramatic side effects, its use was almost dismissed. Many efforts were made in order to design and synthesise new carbazole derivatives with good activity and reduced side effects. The major goal of the present study was to synthesise a series of new N-thioalkylcarbazole derivatives with anti-proliferative effects. Two compounds, 5a and 5c, possess an interesting anti-proliferative activity against breast and uterine cancer cell lines without affecting non-tumoural cell lines viability. The most active compound (5c) induces cancer cells death triggering the intrinsic apoptotic pathway by inhibition of Topoisomerase II.

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

Dey, Nilanjan,Maji, Basudeb,Bhattacharya, Santanu

supporting information, p. 664 - 671 (2018/02/26)

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.

Asymmetric double donor-π-acceptor dyes based on phenothiazine and carbazole donors for dye-sensitized solar cells

Zhu, Bo-ye,Wu, Liang,Ye, Qin,Gao, Jian-rong,Han, Liang

, p. 6307 - 6315 (2017/09/29)

Four organic dyes with asymmetric double donor-π-acceptor system were designed, synthesized and utilized in dye-sensitized solar cells (DSSCs), where phenothiazine and carbazole were introduced as double donors, butyl or octyl chain as the linker and cyanoacetic acid or rhodanine acetic acid as the electron acceptor. The design of double donor-π-acceptor system contributes to a distinctive increase of the molar extinction coefficient and benefits light-harvesting capability of these dyes. Due to superior electron injection efficiency, CPC-series dyes with cyanoacetic acid acceptor exhibit broader IPCE spectra and high IPCE responsive value compared with rhodanine-3-acetic acid acceptor, leading to higher JSC. Long alkyl chain favors antiaggregation effect and low charge recombination rate is observed for dyes with octyl chain which display higher VOC than those with butyl chain. Among four dyes, dye with octyl chain and cyanoacetic acid acceptor exhibits the highest short-circuit photocurrent density (9.64 mA cm?2) and open-circuit photovoltage (720 mV), leading to the best overall power conversion efficiency of 4.76%.

A steam-color-changing nature of the carbazole skeleton bridge chain gold isocyanate compound, preparation and application (by machine translation)

-

Paragraph 0031, (2017/08/25)

The present invention provides a steam-color-changing nature of the carbazole skeleton bridge chain gold isocyanate compound, preparation and application. The formula IV - 1 - 6 of the structure. This kind of compound film of benzene, pyridine, acetone, methylene chloride, toluene, chloroform, tetrahydrofuran, acetonitrile, diethyl ether, ethyl acetate and the like organic solvent vapor of the atmosphere, fluorescent rapidly from a green khaki, showed a sensitive thin film steam color-changing nature. Therefore, such compounds are expected to be present in the environment for future identification or we in the workplace in the harmful volatile chemical solvent. (by machine translation)

Hierarchical manipulation of uniform multi-nanoparticles by electrochemical coupling assembly

Zhang, Jian,Qi, Ji,Kang, Shusen,Sun, Haizhu,Li, Mao

supporting information, p. 5214 - 5219 (2015/05/27)

Assembling multiple nanomaterials into a single nanostructure is a promising way to obtain a multifunctionality derived from each building block. We address here the need for a general all-solution processed strategy to control the fabrication of multiple nanoparticles (NPs) at room temperature and under vacuum free conditions. The monodisperse multiple NPs were integrated successively into thin bulk-hybrid gradient or periodic tandem multilayer films through tuning the cycling number of cyclic voltammetry (CV), which are based on the quantitatively electrochemical deposition of each type of NPs thanks to the electrochemical coupling reaction of the N-alkylcarbazole ligand. This simple method yields nanoporous, transparent, stable and photoactive films with a hierarchical structure of multiple uniform NPs, exemplified by the prototype photodetector devices. Significantly, this strategy opens an avenue to fabricate low-cost wire and 3-dimensional NPs films on physically flexible conducting substrates. This journal is

Carbazole-based gold(i) complexes with alkyl chains of different lengths: Tunable solid-state fluorescence, aggregation-induced emission (AIE), and reversible mechanochromism characteristics

Chen, Zhao,Yang, Lan,Hu, Yuxuan,Wu, Di,Yin, Jun,Yu, Guang-Ao,Liu, Sheng Hua

, p. 93757 - 93764 (2015/11/17)

In this paper, seven carbazole-based mononuclear gold(i) complexes with alkyl chains of different lengths have been synthesized and reported. All of these gold(i) complexes exhibit outstanding AIE characteristics. Furthermore, these various solid-state light-emitting AIE-active gold(i) complexes all show reversible mechanochromic fluorescent behaviors. The possible mechanism explaining these interesting AIE and mechanochromism phenomena involves a variation in weak multiple intermolecular C-H...F and π...π interactions and the formation or alteration of aurophilic interactions.

Structure-activity relationship studies of the chromosome segregation inhibitor, Incentrom A

Lee, Hee-Yoon,Jung, Yongsik,Kim, Wonyeob,Kim, Jin Hee,Suh, Min-Soo,Shin, Seung Koo,Yoon, Hye-Joo

scheme or table, p. 4670 - 4674 (2009/04/08)

A series of Incentrom A analogs that inhibit the chromosome segregation process in yeast were synthesized and tested for their effects on chromosome stability and cell proliferation. Pharmacophore and structure-activity relationship of Incentrom A for the anti-yeast activity were established.

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