544436-46-6

Basic information

• Product Name: 2,7-DibroMo-9-(2-ethylhexyl)-9H-carbazole
• Synonyms: 2,7-DibroMo-9-(2-ethylhexyl)-9H-carbazole;2,7-Dibromo-9-(2-ethylhexyl)carbazole
• CAS NO: 544436-46-6
• Molecular Formula: C₂₀H₂₃Br₂N
• Molecular Weight: 437.21132
• Mol File: 544436-46-6.mol

Chemical Properties

• Melting Point: 100.0 to 104.0 °C
• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,7-DibroMo-9-(2-ethylhexyl)-9H-carbazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,7-DibroMo-9-(2-ethylhexyl)-9H-carbazole(544436-46-6)
• EPA Substance Registry System: 2,7-DibroMo-9-(2-ethylhexyl)-9H-carbazole(544436-46-6)

Safety Data

• Hazardous Substances Data: 544436-46-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Electronics:
2,7-Dibromo-9-(2-ethylhexyl)-9H-carbazole is used as a semiconductor material for its potential applications in organic photovoltaics, light-emitting diodes, and organic field-effect transistors. Its unique structure and properties contribute to the performance and efficiency of these devices.
Used in Optoelectronic Devices:
In the optoelectronics industry, 2,7-Dibromo-9-(2-ethylhexyl)-9H-carbazole is utilized as a key component in the development of advanced light-emitting diodes and other optoelectronic devices, leveraging its semiconductor properties to enhance device performance.
It is important to handle and use 2,7-Dibromo-9-(2-ethylhexyl)-9H-carbazole with caution due to its potentially hazardous nature, ensuring safety protocols are followed in its application across different industries.

Upstream product

• 301-13-3 tris(2-ethylhexyl) phosphite 
• 439797-69-0 4,4'-dibromo-2-nitro-biphenyl 
• 92-86-4 4-(4-bromophenyl)bromobenzene 
• 136630-36-9 4,4′-dibromo-[1,1′-biphenyl]-2,2′-diamine 
• 91371-12-9 4,4'-dibromo-2,2'-dinitrobiphenyl 
• 18908-66-2 3-bromomethylheptane 
• 136630-39-2 2,7-dibromo-9H-carbazole 

Downstream Products

• 862493-91-2 3-benzoyl-2,7-dibromo-N-(2-ethylhexyl)carbazole 
• 862493-92-3 3-(4-tert-butylbenzoyl)-2,7-dibromo-N-(2-ethylhexyl)carbazole 
• 908860-26-4 2,7-bis-(2-acetylphenyl)-9-(2-ethylhexyl)-carbazole 
• 1423186-26-8 6,6'-(5,5'-(9-(2-ethylhexyl)-9H-carbazole-2,7-diyl)bis-(thiophene-5,2-diyl))bis(2,5-bis(2-ethylhexyl)-3-(5-phenylthiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) 
• 476360-83-5 N-(2-ethylhexyl)-2,7-bis(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaboralan-2′-yl)-9H-carbazole 
• 909390-02-9 [C₅H₁₀(C₂H₅)CH₂N(C₆H₃CCPt(C₆H₅)(P(C₂H₅)3)2)2] 
• 1021423-90-4 2,7-di(9-carbazolyl)-9-(2-ethylhexyl)carbazole 
• 908860-29-7 2,7-bis-[2-(2-hydroxyethylphenyl)-9-(2-ethylhexyl)]-carbazole 

Relevant articles and documents

Highly soluble heteroheptacene: A new building block for p-type semiconducting polymers

A facial synthetic route to a new heteroheptacene with the inclusion of carbazole and thiophene units is described. The synthesis of two new semiconducting copolymers with use of the heteroheptacene unit is also reported. The introduction of heteroatoms (sulfur, nitrogen) in the fused-ring system leads to small optical band-gaps of these polymers. The charge carrier mobilities for these polymers are measured in ambient conditions which are sufficient for photovoltaic applications.

Multinuclear 2-(Quinolin-2-yl)quinoxaline-Coordinated Iridium(III) Complexes Tethered by Carbazole Derivatives: Synthesis and Photophysics

Five mono/di/trinuclear iridium(III) complexes (1-5) bearing the carbazole-derivative-tethered 2-(quinolin-2-yl)quinoxaline (quqo) diimine (N^N) ligand were synthesized and characterized. The photophysical properties of these complexes and their corresponding diimine ligands were systematically studied via UV-vis absorption, emission, and transient absorption (TA) spectroscopy and simulated by time-dependent density functional theory. All complexes possessed strong well-resolved absorption bands at 400 nm that have predominant ligand-based 1π,π? transitions and broad structureless charge-transfer (1CT) absorption bands at 400-700 nm. The energies or intensities of these 1CT bands varied pronouncedly when the number of tethered Ir(quqo)(piq)2+ (piq refers to 1-phenylisoquinoline) units, πconjugation of the carbazole derivative linker, or attachment positions on the carbazole linker were altered. All complexes were emissive at room temperature, with 1-3 showing near-IR (NIR) 3MLCT (metal-to-ligand charge-transfer)/3LLCT (ligand-to-ligand charge-transfer) emission at ～710 nm and 4 and 5 exhibiting red or NIR 3ILCT (intraligand charge-transfer)/3LMCT (ligand-to-metal charge-transfer) emission in CH2Cl2. In CH3CN, 1-3 displayed an additional emission band at ca. 590 nm (3ILCT/3LMCT/3MLCT/3π,π? in nature) in addition to the 710 nm band. The different natures of the emitting states of 1-3 versus those of 4 and 5 also gave rise to different spectral features in their triplet TA spectra. It appears that the parentage and characteristics of the lowest triplet excited states in these complexes are mainly impacted by the πsystems of the bridging carbazole derivatives and essentially no interactions among the Ir(quqo)(piq)2+ units. In addition, all of the diimine ligands tethered by the carbazole derivatives displayed a dramatic solvatochromic effect in their emission due to the predominant intramolecular charge-transfer nature of their emitting states. Aggregation-enhanced emission was also observed from the mixed CH2Cl2/ethyl acetate or CH2Cl2/hexane solutions of these ligands.

Organic dyes end-capped with perfluorophenyl anchors: Synthesis, electrochemical properties and assessment of sensitization capacity of titania photoanodes

In the present work, organic sensitizers are synthesized and attached on TiO2 photoanodes via Ti-O-C bonds. All sensitizers, designed for this purpose are symmetrical and have two perfluorophenyl end groups, which can lead to stable non-hydroly

Experimental and Theoretical Investigation for the Level of Conjugation in Carbazole-Based Precursors and Their Mono-, Di-, and Polynuclear Pt(II) Complexes

A series of trimethylsilyl-protected monoalkynes (Me3SiC≡C-R) and bis-alkynes (Me3 SiC≡C-R-C≡CSiMe3) incorporating carbazole spacer groups (R = carbazole-2-yl, carbazole-3-yl, carbazole-2,7-diyl, N-(2-ethylhexyl)carbazole-2,7-diyl, carbazole-3,6-diyl, N-(2-ethylhexyl)carbazole-3,6-diyl), together with the corresponding terminal monoalkynes (H-C≡C-R) and bis-alkynes (H-C≡C-R-C≡C-H), have been synthesized and characterized. The CuI-catalyzed dehydrohalogenation reaction between trans-[(Ph)(Et3P)2PtCl], trans-[(Et3P)2PtCl2], and trans-[(PnBu3)2PtCl2] and the terminal alkynes in iPr2NH/CH2Cl2 affords a series of Pt(II) mono- and diynes, while the dehydrohalogenation polycondensation reactions with trans-[(PnBu3)2PtCl2] under similar reaction conditions yields four Pt(II) poly-ynes of the form trans-[(PnBu3)2Pt-C≡C-R-C≡C-]n. The acetylide-functionalized carbazole ligands and the mono-, di-, and polynuclear Pt(II) σ-acetylide complexes have been characterized spectroscopically, with a subset analyzed using single-crystal X-ray diffraction. The Pt(II) mono-, di-, and poly-ynes incorporating the carbazole spacers are soluble in common organic solvents, and solution absorption spectra show a consistent red-shift between the 2- and 2,7- as well as 3- and 3,6-carbazole complexes. Computational modeling is used to explain the observed spectral shifts, which are related to the enhanced electronic delocalization in the latter systems. These results also indicate that the inclusion of carbazole-2,7-diyl units into rigid-rod organometallic polymers should enhance electronic transport along the chains.

3,6-Carbazole vs 2,7-carbazole: A comparative study of hole-transporting polymeric materials for inorganic-organic hybrid perovskite solar cells

The ever increasing demand for clean energy has encouraged researchers to intensively investigate environmentally friendly photovoltaic devices. Inorganic-organic hybrid perovskite solar cells (PSCs) are very promising due to their potentials of easy fabrication processes and high power conversion efficiencies (PCEs). Designing hole-transporting materials (HTMs) is one of the key factors in achieving the high PCEs of PSCs. We now report the synthesis of two types of carbazole-based polymers, namely 3,6-Cbz-EDOT and 2,7-Cbz-EDOT, by Stille polycondensation. Despite the same chemical composition, 3,6-Cbz-EDOT and 2,7-Cbz-EDOT displayed different optical and electrochemical properties due to the different connectivity mode of the carbazole unit. Therefore, their performances as hole-transporting polymeric materials in the PSCs were also different. The device based on 2,7-Cbz-EDOT showed better photovoltaic properties with the PCE of 4.47% than that based on 3,6-Cbz-EDOT. This could be due to its more suitable highest occupied molecular orbital (HOMO) level and higher hole mobility.

Facile synthesis of a pyrrole-fused dibenzo[a,e]pentalene and its application as a new extended, ladder-type fused aromatic system

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Efficient synthesis of N-alkyl-2,7-dihalocarbazoles by simultaneous carbazole ring closure and N-alkylation

The N-alkyl-2,7-dihalocarbazole as the main product was formed by the reaction of 4,4′-dihalo-2-nitrobiphenyl with aromatic nitro compound and trialkyl phosphite. The presence and crucial role of aromatic nitro compound causes simultaneous carbazole ring closure and N-alkylation unlike the Cadogan ring closure where non-alkylated carbazole is formed as a main product. In addition, the mixture of aromatic nitro compound and trialkyl phosphite was found to be a possible N-alkylating agent for heterocycles, such as carbazole or indole.

High hole mobilities in the amorphous films of 2,7-di(9-carbazolyl)-9-(2- ethylhexyl)carbazole

2,7-Di(9-carbazolyl)-9-(2-ethylhexyl)carbazole was synthesized and investigated as new effective hole-transporting material. The synthesized compound showed high thermal stability with the initial weight loss temperature of 400°C. It forms glass with glass-transition temperature of 88°C. Hole drift mobilities in the amorphous films of the newly synthesized compound exceeded 10-2cm2V-1 s-1 at high electric field, as characterized by the xerographic time of flight technique. Copyright

Multi-Functional Copolymers Comprising Rare Earth Metal Complexes and Devices Thereof

The invention relates to copolymer complexes of the formula (I): wherein [Ax-[B(C)]y-Dz] denotes a single unit of the copolymer complex that is repeated n times, wherein n is an integer greater than one, and wherein the single unit comprises a conjugated backbone coordinated to a complex (C) comprising rare earth metal(s); x, y and z are numbers greater than zero such that x=y+z; A is independently selected from a group consisting of: fluorene, carbazole, oxadiazole, triphenylamine or derivatives thereof; B is a functional ligand selected from the group consisting of: benzoic acid, 1,3-diphenylpropane-1,3-dione, 1,10-phenanthroline, 2,2-bipyridine, or derivatives thereof; and D is independently selected from a group consisting of: fluorene, carbazole, oxadiazole, triphenylamine or derivatives thereof.

Alternating copolymers of N-(2-ethylhexyl)-carbazole derivatives with aniline units: Synthesis and properties

Alternating copolymers such as P(3,6-EHCZ-alt-Al), P(Bis-EHCZ-alt-Al) and P(2,7-EHCZ-alt-Al), based on blue-emitting carbazole and hole-transporting triarylamine units in the polymer backbone, were successfully synthesized by using palladium-catalyzed polycondensation reaction. P(Bis-EHCZ-alt-Al) exhibited blue shift both in UV-Vis absorption and PL emission, while P(2,7-EHCZ-alt-Al) showed red shift in UV-Vis absorption and blue shift in PL emission, compared to P(3,6-EHCZ-alt-Al). It was observed from the optical and electrochemical characterization that band gap energy (2.91～3.07 eV) and HOMO (-5.25～5.11 eV) levels of the copolymers could be fine-tuned by the carbazole content in the repeating unit and different reaction linkage on the carbazole ring.