136630-39-2

Basic information

• Product Name: 2,7-DIBROMO-9H-CARBAZOLE
• Synonyms: 2,7-DIBROMO-9H-CARBAZOLE;2,7-Dibromocarbazole;2,7-Dibromo-9H-carbazole ,97%;9H-Carbazole, 2,7-dibroMo-;N,N-Bis(M-tolyl)benzenaMine,2,7-DibroMo-9H-carbazole, 9H-Carbazole;2,7-DibroMocarbazole (2,7-DBC)
• CAS NO: 136630-39-2
• Molecular Formula: C₁₂H₇Br₂N
• Molecular Weight: 324.99868
• EINECS: 1312995-182-4
• Product Categories: OLED materials,pharm chemical,electronic;carbazole
• Mol File: 136630-39-2.mol
• Article Data: 43

Chemical Properties

• Melting Point: 230.0 to 234.0 °C
• Boiling Point: 459 °C at 760 mmHg
• Flash Point: 231.4 °C
• Appearance: /
• Density: 1.93 g/cm³
• Vapor Pressure: 3.58E-08mmHg at 25°C
• Refractive Index: 1.796
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 15.13±0.30(Predicted)
• CAS DataBase Reference: 2,7-DIBROMO-9H-CARBAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,7-DIBROMO-9H-CARBAZOLE(136630-39-2)
• EPA Substance Registry System: 2,7-DIBROMO-9H-CARBAZOLE(136630-39-2)

Safety Data

• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-45-36/37/39
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: Ⅲ
• Hazardous Substances Data: 136630-39-2(Hazardous Substances Data)

Usage

Application

One of the most popular products made available from 2,7-dibromocarbazole is PCDTBT, a well-known polymer semiconductor used for polymer solar cells. A good example for adjusting the solubility of the carbazole compounds by using 2,7-dibromocarbazole as the starting materials is the synthesis of 2,7-dibromo-9-heptadecanylcarbazole.

Description

2,7-dibromocarbazole, also known as 2,7-dibromo-9H-carbazole, is a building block for the synthesis of small molecules of carbazole series or carbazole back-boned polymers in the application of OFETs, OLEDs, PLEDs and OPVs.

Chemical Properties

White to light yellow powder or crystals

InChI:InChI=1/C12H7Br2N/c13-7-1-3-9-10-4-2-8(14)6-12(10)15-11(9)5-7/h1-6,15H

Upstream product

• 136630-36-9 4,4′-dibromo-[1,1′-biphenyl]-2,2′-diamine 
• 91371-12-9 4,4'-dibromo-2,2'-dinitrobiphenyl 
• 86-74-8 9H-carbazole 
• 301-13-3 tris(2-ethylhexyl) phosphite 
• 439797-69-0 4,4'-dibromo-2-nitro-biphenyl 
• 568592-13-2 2,7-dibromo-9-(4-trimethylsilanylethynylphenyl)-9H-carbazole 
• 92-86-4 4-(4-bromophenyl)bromobenzene 
• 568592-14-3 {4-[7-bromo-9-(4-trimethylsilanylethynylphenyl)-9H-carbazol-2-ylethynyl]phenyl}dimethylamine 
• 568592-10-9 2,7-dibromo-9-(4-nitrophenyl)-9H-carbazole 
• 568592-12-1 2,7-dibromo-9-(4-iodophenyl)-9H-carbazole 
• 568592-11-0 2,7-dibromo-9-(4-aminophenyl)-9H-carbazole 

Downstream Products

• 186192-99-4 2,7-dicyanocarbazole 
• 568592-10-9 2,7-dibromo-9-(4-nitrophenyl)-9H-carbazole 
• 726169-75-1 2,7-dibromo-9-octyl-9H-carbazole 
• 544436-46-6 2,7-dibromo-9-(2-ethyl-hexyl)-9H-carbazole 
• 942207-98-9 4-(2,7-dibromocarbazol-9-yl)benzoic acid methyl ester 
• 444796-09-2 2,7-dibromo-9-(4-phenyl)-9H-carbazole 
• 1292358-49-6 2,7-bis(N-carbazolyl)-N-phenylcarbazole 
• 1256943-90-4 2,7-bis(3,6-di-tert-butyl-9-carbazolyl)-N-phenylcarbazole 
• 1299463-55-0 2,7-bis(diphenylphosphino)-9-phenyl-9H-carbazole 
• 1299463-56-1 (9-phenyl-9H-carbazole-2,7-diyl)bis(diphenylphosphineoxide) 
• 955964-73-5 2,7-dibromo-9-(heptadecane-9-yl)-9H-carbazole 
• 1303532-40-2 N-(4-(2,7-dibromo-9H-carbazol-9-yl)phenyl)-N-phenylbenzenamine 
• 1303991-86-7 2,7-di(1,3,2-dioxaborinan-2-yl)-9-phenyl-9H-carbazole 
• 1303532-42-4 N-(4-(2,7-di(1,3,2-dioxaborinan-2-yl)-9H-carbazol-9-yl)phenyl)-N-phenylbenzenamine 

Relevant articles and documents

Synthesis, Structure and Magnetic Property of a Cobalt(II) Metal-Organic Framework

The three-dimensional (3D) porous cobalt(II) metal-organic framework (MOF), [Co3(L)2(DMA)2(MeOH)2·4(DMA)·6(MeOH)]n (1) [L = fully deprotonated 2,7-bis(4-benzoic acid)-N-(4-benzoic acid) carbazole, DMA = N,N-dimethylacetamide], was synthesized by hydrothermal reaction. Based on X-ray single-crystal diffraction, structural analysis indicates that complex 1 crystallizes in the monoclinic C2/c space group. Complex 1 possesses a 3,6-connected three-dimensional (3D) topological structure with a point symbol of {42·6}2{44·62·87·102} when a trinuclear CoII cluster was regarded as 6-connected node and the organic ligands could be regarded as 3-connected linkers between the 6-connected nodes. The framework structure exhibits a one-dimension (1D) channel with an accessible void of 4223.0 ?3, amounting to 42.8 % of the total unit-cell volume (9862.0 ?3). Moreover, the magnetic properties of complex 1 were studied.

Efficient Synthesis of 2,7-Dibromocarbazoles as Components for Electroactive Materials

An efficient two-step synthesis of 2,7-dibromocarbazole is reported. Nitration and Friedel-Crafts acylation of 2,7-dibromocarbazole proceed readily at the activated 3 and 6 positions to give new multifunctionalised carbazoles, which are of interest as monomers for new electrically active organic materials.

Conjugated polymers with carbazole, fluorene, and ethylene dioxythiophene in the main chain and a pendant cyano group: Synthesis, photophysical, and electrochemical studies

Six new conjugated polymers comprising of carbazole, fluorene, and ethylene dioxythiophene (EDOT) moieties along the backbone with a pendant cyano group attached to the ethylene moiety have been designed and synthesized via Sonogashira coupling polymerization reaction. Optical and electrochemical characterizations have shown that the energy band gaps lie within the range of 2.35–2.44 eV. Additionally, the presence of carbazole and EDOT makes these polymers better hole transporting materials, which is reflected from their low oxidation potential peaks (0.55–1.11 V) in cyclic voltammograms. Furthermore, the aggregation enhanced emission (AEE) phenomenon resulted in a 2.6-fold increase in fluorescence intensity in a 90:10 THF/water mixture in comparison to pristine THF. The AEE properties were further verified by DLS (dynamic light scattering) experiment and SEM (scanning electron microscopy) studies. Polymers in solution as well as in polystyrene matrix emit in the green region (quantum yield in solution state Φf =41–43%) with CIE values (0.25–0.36, 0.52–0.57). Excellent thermal stability is observed for the new polymers.

Simple synthesis and molecular engineering of low-cost and star-shaped carbazole-based hole transporting materials for highly efficient perovskite solar cells

Perovskite solar cells (PrSCs) have emerged as a very promising technology in the field of photovoltaics by demonstrating power conversion efficiencies (PCEs) soaring from 3.9% to above 22% within the past eight years. To date, perovskite solar cells mainly depend on spiro-OMeTAD to perform a key role as a hole transporting material (HTM). However, the complicated multi-step synthetic procedures and high-cost purification process for spiro-OMeTAD limited its potential for commercial application. Herein, three new carbazole-based HTMs with a starburst structure, coded as SGT-405(3,6), SGT-410(3,6) and SGT-411(3,6) via tuning the substitution position from the (2,7) to the (3,6) position of the carbazole moiety, have been successfully synthesized via three-step synthesis from commercially available reagents and investigated for highly efficient perovskite solar cells. By adopting this strategy, among them, molecularly engineered carbazole derivative SGT-405(3,6) exhibits significantly increased Tg (192.7 °C), improved film forming ability, reduced hole reorganization energy and enhanced hole mobility compared to its parent molecule SGT-405(2,7) and spiro-OMeTAD. Owing to the promising properties of SGT-405(3,6), meso-porous type PrSCs employing SGT-405(3,6) showed a remarkable PCE of 18.87%, which is better than that of the photovoltaic device employing spiro-OMeTAD (17.71%). To the best of our knowledge, the achieved PCE (18.87%) is the highest value reported for devices with the structure of FTO/compact TiO2/meso-porous TiO2/CH3NH3PbI3-xClx/HTM/Au employing small-molecular HTMs. Meanwhile, owing to the simple synthesis of SGT-405(3,6), compared with SGT-405(2,7) previously developed by our group, synthesis cost was much lowered, resulting in low cost compared to the spiro-OMeTAD and SGT-405(3,6), by approximately three times. Furthermore, the long-term device stability of PrSCs was enhanced for SGT-405(3,6) to some extent compared to those of other HTMs studied here due to the good uniform capping layer of SGT-405(3,6) on top of the perovskite layer and the prevention of moisture penetration into the perovskite layer. Therefore, SGT-405(3,6) is a promising low-cost and efficient non-spiro type HTM with potential to replace expensive spiro-OMeTAD for PrSCs.

Fluorescence behavior of a unique two-photon fluorescent probe in aggregate and solution states and highly sensitive detection of RNA in water solution and living systems

It is found that 2,7-substituted carbazole derivative HVC-6 possesses distinct luminescence features in both aggregate and solution states. In view of this, probe HVC-6 realizes highly sensitive detection of RNA in pure water systems by an aggregation-disaggregation method for the first time.

Syntheses, structures, luminescence and magnetic properties of seven isomorphous metal-organic frameworks based on 2,7-bis(4-benzoic acid)-: N -(4-benzoic acid)carbazole

We report herein seven novel lanthanide metal-organic frameworks (Ln-MOFs), [M(L27)(DMA)(H2O)·XH2O]n (TCZ-M), (M = Nd, Sm, Eu, Gd, Tb, Dy, Ho), (X = 2 or 3) (H3L27 = 2,7-bis(4-benzoic acid)-N-(4-benzoic acid)carbazole, DMA = N,N-dimethylacetamide, TCZ = "T"-shape carbazole-based MOFs, L27 = fully deprotonated H3L273- ligand). X-ray crystallography showed that all the TCZ-M (M = Nd, Sm, Eu, Gd, Tb, Dy, Ho) are isomorphous and possess a 3,6-connected three-dimensional (3D) framework with a point symbol of {4·62}2{42·610·83}. The photoluminescence measurement indicates that TCZ-Eu shows reddish-orange emission bands and TCZ-Sm shows both visible and near-infrared (NIR) emission bands. Magnetic susceptibility measurements show deviations from the Curie law mainly owing to the split of the ground term due to the ligand field and spin-orbit coupling in TCZ-Eu and TCZ-Sm. The magnetic properties of TCZ-M (M = Nd, Gd, Tb, Dy, Ho) are also investigated, and the results indicate a ferromagnetic interaction between the Tb3+ magnetic centers in TCZ-Tb and the antiferromagnetic interactions in TCZ-M (M = Nd, Gd, Dy, Ho).

Red organic electroluminescent material and preparation method thereof

The invention belongs to the technical field of photoelectric display devices, and particularly relates to a red organic electroluminescent material and a preparation method thereof. The invention provides the red light organic electroluminescent material, the structure of which is represented by formula (I): wherein R is a hydrogen atom, a linear chain or branched chain alkyl group with a carbonatom number of 1-20, x is 0-1, and the polymerization degree n is 3-800. The invention also provides a preparation method of the red light organic electroluminescent material. The preparation method comprises that 2', 7 '-dibromo-1, 2, 7, 8-tetraoctyl-9'-spiro-bis[fluorene], 2, 2'-(1', 2 ', 7', 8 '-tetraoctyl-9, 9'-spiro-bis [fluorene]-2, 7-diyl)bis(4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborane) and3, 10-dibromo-14-(3-(5-phenyl-1, 3, 4-oxadiazole-2-yl) phenyl)-14H-bis (S, S-dioxo-dibenzothiophene)pyrrole undergo a Suzuki coupling reaction to produce a polymer shown as a formula (I). The red light organic electroluminescent material and the preparation method thereof provided by the invention solve the technical problem of poor electroluminescent performance of the existing red-light polymer.

Double-(S, S - dioxo - dibenzo thiophene) and high output compound and its preparation method and application

The invention discloses a bi(S,S-dioxo-dibenzothiophene) five-membered ring compound and a preparation method and application thereof. The existence of bi-sulfuryl in the bi(S,S-dioxo-dibenzothiophene) five-membered ring compound is more beneficial for improving the electron affinity of molecules. Alkyl chains are introduced on a five-membered ring, so that the solubility of monomers in an organic solvent can be obviously improved. The plane conjugacy of the compound is better, and is beneficial for the transmission of a current carrier. Higher D-A mutual effect existing in the molecules of the compound endows higher fluorescence of the material. The bi(S,S-dioxo-dibenzothiophene) five-membered ring compound is synthesized and obtained through common organic chemistry reactions such as substitution reactions, Suzuki coupling and ring-closure reactions and oxidation reactions. The compound has good solubility in the organic solvent, and is suitable for solution processing. The compound has wide application prospects in the fields of organic luminescence display, organic photovoltaic cells and organic field-effect tubes.